Month: November 2020

103946-54-9, 4′-Methyl-[2,2′-bipyridine]-4-carboxylic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

103946-54-9, 4,4′-Dimethyl-2,2′-bipyridine (1.5 g, 8 mmol) and selenium dioxide (887.68 mg, 8 mmol) were refluxed in 100 ml of 1,4-dioxane for 24 hours, after cooling to room temperature, the black solid was filtered off and solvent was removed by evaporation to give a white solid. This solid was dissolved by stirring with 100 ml of ethyl acetate, the insoluble material was filtered off, and the filtrate was washed three times with 20 ml of a 1.0 M sodium carbonate solution. The organic phase was extracted three times with 50 ml of 0.3 M sodium metabisulfite solution, the aqueous phase was combined, the pH was adjusted to 10 with sodium carbonate solution, and extracted four times with 20 ml of chloroform, the organic phase was combined, which was dried over anhydrous sodium sulfate and solvent was removed by evaporation to give a crude product. The crude product was purified by column chromatography eluting with petroleum ether / ethyl acetate (1: 4) to give aldehyde-substituted bipyridine 398 mg was obtained in a yield of 25%. The aldehyde-substituted bipyridine was dissolved in 20 ml of ethanol, stirred with 4 ml of a silver nitrate aqueous solution, then 10 ml of a 1.0 M aqueous sodium hydroxide solution was slowly added and reacted at room temperature for 15 hours. The solvent was removed by evaporation and the solid was washed twice with 4 ml of 1.3 M sodium hydroxide and 4 ml of water, the combined filtrate was extracted three times with 10 ml of chloroform, aqueous phase pH was 3.5 with 4 M hydrochloric acid, the resulting white solid was filtered and dried in vacuo to give carboxy-substituted bipyridine 258 mg, yield 60%. The resulting carboxyl substituted bipyridine (1.3 mmol) was all dissolved in 20 ml DMF, then aminothiazole compound (300 mg, 1.3 mmol), 1-hydroxy-7-azobenzotriazole (1.3 mmol, 177 mg), 4-dimethylaminopyridine (1.3 mmol, 146 mg), 1-ethyl-carbonyldiimide hydrochloride (1.3 mmol, 87 mg) were added thereto, and stirred at room temperature for 6 hours. The obtained solid was filtered, washed four times with 25 ml of water and dried in vacuo to give the Aminothiazole functional group-substituted polypyridine ligand (L1) 457 mg, yield 82%. All the obtained L1 (1.06 mmol) and the compound cis-[Ru(bpy)2Cl2].2H2O (442 mg, 0.85 mmol) were refluxed under 20 ml of ethylene glycol and argon gas protection for 8 hours. After cooling to room temperature, 10 ml of a saturated aqueous solution of ammonium hexafluorophosphate was added,the obtained orange precipitate was filtered, washed once with 15 ml of water, washed three times with 30 ml of anhydrous diethyl ether and dried in vacuo to give crude product. The crude product is subjected to neutral alumina column chromatography, and the only orange component is eluted with acetonitrile to obtain the target polypyridyl ruthenium complex Ru1, amount 616 mg, yield 64%

103946-54-9 4′-Methyl-[2,2′-bipyridine]-4-carboxylic acid 11127621, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Yunnan University; Gao Feng; Yan Ru; Bi Xudan; (15 pag.)CN109232663; (2019); A;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

To a stirred solution of 2,4 dimethoxy benzaldehyde (0.542 g, 3.3 mmol) in tetrahydrofuran (10 ml.), was added N, N-diisopropyl ethyl amine (1.0 g, 7.0 mmol) followed by the addition of (25,5 ?)-N-(2-hydrazino-2-oxoethyl)-7-oxo-6-(sulfooxy)- l,6-diazabicyclo [3.2.1 ]octane-2- carboxamide (1 g, 3.0mmol) at 25C. The reaction mixture was stirred for 16 hours and to the resulting mixture was added a solution of tetrabutylammonium acetate (0.3 g, 3.0 mmol) in tetrahydrofuran (10 ml.) and stirring continued further for 24 hours. The solvent was evaporated under reduced pressure and the residue was taken up in dichloro methane (20 ml) and washed with 10% aqueous potassium hydrogen sulfate solution (3 ml x 2) and finally organic layer was washed with water (5 ml). The organic layer was separated and dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield a semi solid residue. This was purified by column chromatography over silica-gel (60- 120 mesh) by eluting with mixture of methanol in dichloro methane (5: 95). The combined fractions were evaporated under reduced pressure to obtain 1.1 g of tetrabutylammonium salt of (25,5 ?)-N-{2-[(2E,Z)-2-(2,4-dimethoxybenzylidenehydrazino]-2-oxoethyl}-7-oxo-6-(sulfooxy)- l,6- diazabicyclo[3.2.1]octane-2-carboxamide as a white solid in 51%

10534-59-5, 10534-59-5 Tetrabutylammonium acetate 82707, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; WOCKHARDT LIMITED; PATIL, Vijaykumar Jagdishwar; TADIPARTHI, Ravikumar; LOGANANTHAN, Velupillai; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; PAWAR, Mangesh; PATEL, Piyush Ambalal; JOSHI, Prashant Ratnakar; PATEL, Mahesh Vithalbhai; (57 pag.)WO2017/2089; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14162-95-9,4-Bromo-2,2′-bipyridine,as a common compound, the synthetic route is as follows.,14162-95-9

General procedure: In a tube were added 6-bromo-2,2-bipyridine (70.5mg, 0.3mmol, 1equiv.), phenothiazine (77.7mg, 1.3equiv.), RuPhos-Pd-G2 (23.4mg, 10mol%) and t-BuOK (50.5mg, 1.5equiv). The tube was sealed, purged three times with argon and 1mL of anhydrous dioxane was added. The reaction mixture was stirred at 110C for 18h. After cooling to room temperature, 10mL of H2O were added and the aqueous layer was extracted three times with ethyl acetate (3¡Á10 mL). The combined organic layers were dried with MgSO4 and the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (50/50: CH2Cl2/cyclohexane) affording 51.2 mg of L1 (0.145 mmol, 48%) as an amorphous pale yellow solid.

As the paragraph descriping shows that 14162-95-9 is playing an increasingly important role.

Reference£º
Article; Tabey, Alexis; Mendy, Jonathan; Hermange, Philippe; Fouquet, Eric; Tetrahedron Letters; vol. 58; 32; (2017); p. 3096 – 3100;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

170161-27-0, Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A solution of 2,6-bis(bromomethyl)quinolineS7 (63.7 mg, 200 mumol) was added to solution of tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate (101 mg, 200 mumol), bis(pyridin-2-ylmethyl)amine (40.3 mg, 200 mumol) and K2CO3 (55.9 mg, 200 mumol) in CH3CN (2.50 mL) under N2 and stirred at 80 C for 48 h under microwave irradiation. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc. The organic layer was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to obtain the corresponding tri-N-Boc-protected amine intermediates. The intermediates were then dissolved in CHCl3 (2.50 mL) and treated with 95% aqueous TFA (2.50 mL) at 0 C for 6 h. The mixture was concentrated under reduced pressure and purified by preparative HPLC to obtain the desired compounds with the mixture of regioisomers 23AB., 170161-27-0

170161-27-0 Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate 10940041, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Sakyiamah, Maxwell M.; Kobayakawa, Takuya; Fujino, Masayuki; Konno, Makoto; Narumi, Tetsuo; Tanaka, Tomohiro; Nomura, Wataru; Yamamoto, Naoki; Murakami, Tsutomu; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 27; 6; (2019); p. 1130 – 1138;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

338-69-2, H-D-Ala-OH is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: SOCl2 (21.8mL, 0.3mol) and (S)-alanine ((S)-19, 8.91g, 0.1mol) were added to CH3OH (100mL) and the mixture was stirred at RT for 2h. The solvent was removed in vacuo, the residue was dissolved in methanol (30mL) and the organic solvent was removed in vacuo again. This procedure was repeated twice. Colorless amorphous solid, mp 103C (Ref. 39 mp 98-99C), yield 14.3g (>99%)., 338-69-2

As the paragraph descriping shows that 338-69-2 is playing an increasingly important role.

Reference£º
Article; Fanter, Lena; Mueller, Christoph; Schepmann, Dirk; Bracher, Franz; Wuensch, Bernhard; Bioorganic and Medicinal Chemistry; vol. 25; 17; (2017); p. 4778 – 4799;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4199-88-6,5-Nitro-1,10-phenanthroline,as a common compound, the synthetic route is as follows.

Complex 1 was prepared by a conventional synthetic method, in which a mixture ofdichloromethane and methanol (42 mL, 2:1) was added to a flask containing [Ir(Hppy)2Cl]2 (0.323 g,0.30 mmol) and NP (0.135 g, 0.60 mmol) [19]. The mixture was refluxed for 6 h under argon to givea red brown solution. After cooling, a bright red precipitate was obtained by dropwise additionof concentrated NH4PF6 aqueous solution with stirring at room temperature for 2 h. The crudeproduct was purified by column chromatography on alumina eluted with dichloromethane-acetone(1:3, v/v). The red band was collected, the solvent was evaporated under the reduced pressure, and abrown-yellow powder was obtained. Yield: 86%. Anal. Calc for C34H23F6N5O2PIr: C, 46.90; H, 2.66;N, 8.04%. Found: C, 46.81; H, 2.72; N, 8.12%. 1H NMR (500 MHz, DMSO-d6): 9.46 (s, 1H), 9.20 (d, 1H,J = 8.0 Hz), 9.12 (d, 1H, J = 7.5 Hz), 8.34 (dd, 2H, J = 5.5, J = 6.0 Hz), 8.26 (d, 2H, J = 8.0 Hz), 8.19-8.15(m, 2H), 7.95 (d, 2H, J = 8.0 Hz), 7.88 (t, 2H, J = 7.5 Hz), 7.52 (dd, 2H, J = 6.0, J = 6.0 Hz), 7.06 (t, 2H,J = 7.5 Hz), 7.01-6.94 (m, 5H), 6.26 (d, 2H, J = 7.5 Hz). 13C NMR (125 Hz, DMSO-d6): 166.70, 153.41,151.88, 149.56, 149.11, 147.87, 146.79, 144.96, 144.04, 140.80, 138.87, 135.24, 131.23, 130.33, 128.52, 128.34,127.45, 125.14, 123.97, 123.89, 122.60, 120.03. ESI-MS (CH3CN): m/z 725.9 ([M-PF6]+)., 4199-88-6

As the paragraph descriping shows that 4199-88-6 is playing an increasingly important role.

Reference£º
Article; Zhang, Li-Xia; Gu, Yi-Ying; Wang, Yang-Jie; Bai, Lan; Du, Fan; Zhang, Wen-Yao; He, Miao; Liu, Yun-Jun; Chen, Yan-Zhong; Molecules; vol. 24; 17; (2019);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 2 or 3 (0.50 mmol), the corresponding acids RCOOH (0.60 mmol),DCC (0.60 mmol), DMAP (0.1 mmol) in dry dichloromethane (15 mL) was stirred atroom temperature. When the reaction was completed, and checked by TLC, the mixturewas filtered to remove urea from the reaction, and the filtrate was diluted bydichloromethane (45 mL). Subsequently, the diluted organic phase was washed bysaturated aqueous NaHCO3 (30 mL), and brine (30 mL), dried over anhydrousNa2SO4, concentrated in vacuo, and purified by CC to give the pure 9R/S-acyloxyderivatives of cinchonidine and cinchonine 5a-j,l-o and 6a,c,e-o [17-19]. The dataof target compounds are shown as follows.

485-71-2, The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Che, Zhi-Ping; Chen, Gen-Qiang; Jiang, Jia; Lin, Xiao-Min; Liu, Sheng-Ming; Sun, Di; Tian, Yue-E; Yang, Jin-Ming; Zhang, Song; Journal of Asian Natural Products Research; (2020);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

391604-55-0, 2-(2,4-Difluorophenyl)pyridine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium (I) chloride dimer (2.00 g, 2.98 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (20 mL, s/s=10) and 2-(2,4-difluorophenyl)pyridine (3.42 g, 17.88 mmol, 6.0 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C). Immediately after the addition of the ligand (2-(2,4-difluorophenyl)pyridine), the reddish suspension turned into gray and then into a dark reddish solution as the dissolution of the ligand by heating, which gave an lemon yellow suspension with stirring. After stirring for 3 hours, the solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 10/1). The column fractions were condensed, and the resulting yellow green solid material was recrystallized from hexane/dichloromethane to give 3. 53 g of the title compound (2-10) as yellow green powder in 97.4% yield. 1H NMR (500MHz CD2Cl2) : delta 5.29 (dd, J=2.5, 9.1 Hz, 4H), 6.38 (ddd, J=2.5, 9.1, 12.5Hz, 4H), 6.87 (ddd, J=1.5, 5.8, 7.2Hz, 4H), 7.87 (ddd, J=1.5, 5.8, 7.2Hz, 4H), 8.33 (ddd, J=0.7, 1.5, 8.1Hz, 4H), 9. 12 (ddd, J=0.7, 1.5, 5.8Hz, 4H).; Example 6 Production of Compound (3-10) (Bis[2-(2,4-difluorophenyl)pyridinato-N,C2′]iridium (III) acetylacetonate) (1) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0.744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s = 10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting lemon yellow suspension was cooled to room temperature, to which were added acetylacetone (230muL, 2.232 mmol, 3.0 equivalents) and sodium carbonate (237 mg, 2.232 mmol, 3.0 equivalents) successively, and further stirred under refluxing for 2 hours to give an yellow suspension. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and recrystallized from hexane/dichloromethane to give 896 mg of the title compound (3-10) as lemon yellow powder in 78.9%. 1H NMR (500MHz, CD2Cl2) : delta 1.80 (s, 6H), 5.31 (s, 1H), 5.50 (dd, J=2.4, 8.8Hz, 2H), 6.38 (ddd, J=2.4, 9.3, 12.5Hz, 2H), 7.24 (ddd, J=1.5, 5.7, 7.3Hz, 2H), 7.84 (ddt, J=0.6, 1.6, 7.3Hz, 2H), 8.22-8.28 (m, 2H), 8.44 (ddd, J=0.8, 1.6, 5.7Hz, 2H).; Example 10 Production of Compound (4-2) (Bis[2-(2,4-difluorophenyl)pyridinato-N,C6′]iridium (III) picolinate) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium (I) chloride dimer (500 mg, 0.744 mmol, 1.0 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 ml, s/s=10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting lemon yellow suspension was cooled to room temperature, to which was added sodium picolinate (324 mg, 2.232 mmol, 3.0 equivalents), and further stirred under refluxing for 3 hours. The suspension slowly turn into orange with proceeding of the reaction. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 20/1). The column fractions were condensed, and the resulting yellow solid was recrystallized from hexane/dichloromethane to give 967 mg of the title compound (4-2) as lemon yellow powder in 93.6% yield. 1H NMR (500MHz CD2Cl2) delta 5.62 (dd, J=2.4, 8.7Hz, 1H), 5.85 (dd, J=2.4, 8.7Hz, 1H), 6.44 (ddd, J=2.4, 9.2, 12.6Hz, 1H), 6.50 (ddd, J=2.4, 9.2, 12.6Hz, 1H), 7.02 (ddd, J=1.5, 5.9, 7.4Hz, 1H), 7.21 (ddd, J=1.5, 5.9, 7.4Hz, 1H), 7.40 (ddd, J=1.5, 5.4, 7.6Hz, 1H), 7.46 (ddd, J=0.8, 1.6, 5.9Hz, 1H), 7.75-7.86 (m, 3H), 7.94 (dt, J=1.5, 7.6Hz, 1H), 8.20-8.28 (m, 2H), 8.28-8.37 (m, 1H), 8.69 (ddd, J=0.7, 1.6, 5.9Hz, 1H).; Example 12 Production of Compound (5-6) (tris [2-(2,4-difluorophenyl)pyridinato-N,C6′]iridium(III)) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0.744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s=10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting yellow green suspension was cooled to room temperature, to which w…

391604-55-0, As the paragraph descriping shows that 391604-55-0 is playing an increasingly important role.

Reference£º
Patent; TAKASAGO INTERNATIONAL CORPORATION; WO2004/43974; (2004); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

119-91-5, 2,2′-Biquinoline is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1 (0.332 g, 1.0 mmol) and CuI (0.191 g, 1.0 mmol) were dissolved in 5 ml CHCl3. After a few minutes, bq (0.257 g, 1.0 mmol) in 10 ml CHCl3 was added. The mixture was stirred at 40 C for 2 h. After this time, a burgundy solution was formed. Then the solvent was evaporated to dryness. A dark red solid was crystallized from CHCl3 to give microcrystals which are soluble in CHCl3, CH2Cl2, THF, DMSO, CH3CN and CO(CH3)2. Yield 52%. Anal. Calc. for C33H42CuIN5O3P: C, 50.94; H, 5.44; N, 9.00. Found: C, 50.78; H, 6.02; N, 8.91%. MS (CHCl3): 575.1 [Cu(bq)2]+ 100%, 319.0 [Cu(bq)]+ 13%, 650.2 [Cu(bq)1]+ 10%. NMR (298 K, CHCl3) 31P{1H}: -28 s?; 1H: 8.21 s? (H3), 7.95-7.80 (H4 and H7), 7.65-7.55 (H5 and H6), 9.19 s? (H8), 2.78 s (H1-P), 2.40 s? (H2-P), 3.43 s? (H3-P); 13C{1H}:119.39 s (C1, C3), 137.63 s (C4), 128.01 s (C5), 127.53 s (C6), 130.22 s (C7), 130.93 s (C8), 146.42 s (C9), 128.61 s (C10), 55.18 s? (C1-P), 55.57 s (C2-P), 66.74 s (C3-P)., 119-91-5

As the paragraph descriping shows that 119-91-5 is playing an increasingly important role.

Reference£º
Article; Starosta, Rados?aw; Brzuszkiewicz, Anna; Bykowska, Aleksandra; Komarnicka, Urszula K.; Bazanow, Barbara; Florek, Magdalena; Gadza?a, ?ukasz; Jackulak, Natalia; Krol, Jaros?aw; Marycz, Krzysztof; Polyhedron; vol. 50; 1; (2013); p. 481 – 489;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

153-94-6, H-D-Trp-OH is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 19 Preparation of H-D-Glu(D-Trp-0-CH(CH3)0-CO-0-cyclohexyl)-0-Et hydrochloride salt, Apo854.HCI Cbz-D-Glu(OH)-0-Et (12.1 g, 39.1 mmol), HOSu (4.60 g, 40.0 mmol) andEDCI.HCI (7.67 g, 40.0 mmol) were mixed in DMF (100 mL) under ice-water bath temperature. The reaction mixture was allowed to warm to RT then stirred for overnight. The reaction mixture was cooled again in an ice-water bath and D-Trp- OH (8.17 g, 40.0 mmol) was added. The mixture was stirred at room temperature for overnight. The mixture was poured into a beaker containing 0.5N HCI (200 mL) and ice pellets. The mixture was extracted with ethyl acetate (2×200 mL + 1×100 mL). The organic layers were combined and washed with a 0.5N HCI solution (100 mL), water (2×100 mL) and brine (100 mL), dried over MgS04, then filtered. The filtrate was concentrated via rotary evaporation under reduced pressure and the resulting solid Cbz-D-Glu(D-Trp-OH)-0-Et was triturated with10% ethyl acetate in hexanes. The precipitated white solid was collected via suction filtration (17.6 g). Yield = 90 %; 1H NMR (DMSO-D6l 400 MHz) delta ppm: 12.58 (br. s, 1 H), 10.82 (s, 1H), 8.12 (d, J = 8.1 Hz, 1 H), 7.71 (d, J = 8.1 Hz, 1 H), 7.52 (d, J = 8.1 Hz, 1H), 7.23 – 7.42 (m, 6H), 7.12 (s, 1 H), 7.06 (t, J = 7.6 Hz, 1 H), 6.97 (t, J = 7.6 Hz, 1H), 4.97 – 5.10 (m, 2H), 4.41 – 4.51 (m, 1H), 3.95 – 4.15(m, 3H), 3.15 (dd, J = 14.1 , 5.1 Hz, 1H), 2.99 (dd, J = 15.2, 8.1 Hz, 1 H), 2.09 – 2.26 (m, 2H), 1.83 – 1.96 (m. 1 H), 1.65 – 1.81 (m, 1 H), 1.16 (t, J – 7.1 Hz, 3H); MS-ESI (m/z): 496 [ +1f. To a mixture of Cbz-D-Glu(D-Trp-OH)-0-Et {4.95 g, 0.0 mmol) with potassium carbonate (4.15 g, 30.0 mmol) and sodium iodide (6.00 g, 40.0 mmol) in Lambda/,/V-dimethylformamide (30 mL) at room temperature, 1-chtoroethylcyclohexyl carbonate (6.20 g, 30.0 mmol) was added. After being stirred at room temperature for overnight, additional W,/V-dimethylformamide (30 mL) was added and the reaction mixture was stirred at 40C for overnight. The reaction mixture was diluted with ethyl acetate then washed with water (3x) then with brine. The crude product Cbz-D-Glu(D-Trp-0-CH(CH3)-0-CO-0-cyclohexyl)-0-Et was purified by column chromatography on silica gel using a solvent gradient of a mixture of ethyl acetate in hexanes (20 to 40%) as eluant. Fractions rich in product were combined together and evaporated to dryness. Thus, the desired compound Cbz-D-Glu(D-Trp-0-CH(CH3)-0-CO-0-cyclohexyl)-0-Et (4.43 g) was obtained as a pale-yellow foam. Yield = 66 %; 1H NMR (DMSO-D6> 400 MHz) delta ppm: 10.86 (or. s, 1H), 8.36 (dd, J = 17.2, 7.1 Hz, 1 H), 7.66 – 7.77 (m, 1 H), 7.46(t, J = 8.0 Hz., 1H), 7.22 – 7.42 (m, 6H), 7.10 – 7.20 (m, 1 H), 7.02 – 7.10 (m, 1 H), 6.90 – 7.02 (m, 1 H), 6.58 – 6.70 (m, 0.5H), 6.46 – 6.58 (m, 0.5H), 5.04 (br. s, 2H), 4.38 – 4.61 (m, 2H), 3.93 – 4.15 (m, 3H), 2.90 – 3.17 (m, 2H), 2.20 (br. s, 2H), 1.54 – 1.96 (m, 6H), 1.02 – 1.53 (m, 12H); MS-ESI (m/z): 666 [M+1f. Cbz-D-Glu(D-Trp-0-CH(CH3)-0-CO-0-cyclohexyl)-0-Et (2.0 g, 3.0 mmol) and 10 % Pd/C (wet, 0.6 g) was mixed in ethanol (50 mL) and 2 HCI in ether (1.7 mL, 3.4 mmol). The reaction mixture was hydrogenated in a Parr apparatus at 20-25 psi of hydrogen pressure for an hour. The mixture was filtered through Celite and the cake was washed with ethanol. The filtrate was concentrated by rotary evaporation and the residue was triturated with a mixture of ether and hexanes. Thus, H-D-Glu(D-Trp-O-CH(CH3)-0-CO-0-cyclohexyl)-0-Ethydrochloride salt (Apo854.HCI, 0.80 g) was obtained as a pink solid foam. Yield = 47%; *H NMR (DMSO-D6, 400 MHz) delta ppm: 0.94 (br. s, 1 H), 8.57 (br. s, 4H), 7.47 (t, J = 8.1 Hz, 1H), 7.34 (d, J = 8.1 Hz, 1H), 7.19 (s, 1 H), 7.07 (t, J = 7.6 Hz, 1 H), 6.88 – 7.03 (m, 1 H), 6.58 – 6.72 (q, J = 5.1 Hz, 0.5H), 6.53 (q, J = 5.1 Hz,0.5H), 4.39 – 4.63 (m, 2H), 4.00 – 4.26 (m, 2H), 3.78 – 4.00 (m, 1 H), 2.93 – 3.18 (m, 2H), 2.18 – 2.41 (m, 2H), 1.88 – 2.02 (m, 2H), 1.82 (br. s, 2H), 1.63 (br. s, 2H), 1.13 – 1.53 (m, 12H); MS-ESI (m/z): 532 [M+1]+ (free base).

153-94-6, 153-94-6 H-D-Trp-OH 9060, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; APOTEX TECHNOLOGIES INC.; TAM, Tim, Fat; LEUNG-TOUNG, Regis; WANG, Yingsheng; ZHAO, Yanqing; XIN, Tao; LI, Wanren; WODZINSKA, Jolanta, Maria; RABADIA, Vrajlal, S.; FEENEY, Christopher, John; WO2012/129671; (2012); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI