Category: 153-94-6

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.153-94-6,H-D-Trp-OH,as a common compound, the synthetic route is as follows.

General procedure: 5-Bromothiophene-2-sulfonylchloride (1g, 4.43 mmol) was added to a solution of the appropriate non-natural commercial amino acid (4.43 mmol) in H2O (4.43 mL) and dioxane (13.3 mL) containing Et3N (1.24 mL, 8.86 mmol). The mixture was stirred at room temperature overnight, the dioxane was evaporated and the residue was treated with EtOAc and washed with HCl 1 N and brine. Organic layers were then collected, dried over Na2SO4, and evaporated in vacuo.

153-94-6, As the paragraph descriping shows that 153-94-6 is playing an increasingly important role.

Reference£º
Article; Nuti, Elisa; Casalini, Francesca; Santamaria, Salvatore; Gabelloni, Pamela; Bendinelli, Sara; Da Pozzo, Eleonora; Costa, Barbara; Marinelli, Luciana; La Pietra, Valeria; Novellino, Ettore; Margarida Bernardo; Fridman, Rafael; Da Settimo, Federico; Martini, Claudia; Rossello, Armando; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2617 – 2629;,
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

General procedure: To 4mL of ice-bath cooled methanol was added drop-wise 1mL of thionyl chloride in 5min under nitrogen, the resulting mixture was stirred for 0.5h and amine derivatives 3a-3f were added. The reaction mixture was stirred at room temperature overnight until complete disappearance of the materials indicated by TLC. The solvent and the surplus SOCl2 were removed in vacuum. The residue was dissolved in 20mL of methanol and evaporated under reduced pressure. The procedure was repeated for three times. Then 20mL of ether was added to the residue and evaporated in vacuum, which also took three times. Target compounds 4a-4f were obtained in 86%-95% yield and used without further purification for the following step., 153-94-6

As the paragraph descriping shows that 153-94-6 is playing an increasingly important role.

Reference£º
Article; Tang, Hong-Jin; Zhang, Xiao-Wei; Yang, Lin; Li, Wei; Li, Jia-Huang; Wang, Jin-Xin; Chen, Jun; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 637 – 648;,
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

To a suspension of (R)-2-Amino-3-(lH-indol-3-yl)-propionic acid 2 (0.23 g, 1.12 mmol) (Alfa-Aesar, A- 18426) in acetone (3 mL) was added 2M sodium carbonate (1 mL) to stir at room temperature for 30 minutes. To this mixture was added bromosulfonyl chloride 1 (0.13g, 0.5 mmol) (Alfa-Aesar, A-14677) at 0 0C to stir for 15 minutes. The reaction mixture was stirred further for 1 hour at room temperature. After pouring into water (20 mL), the solution was washed with ether (x3). The aqueous layer was acidified with IM HCl, followed by extraction with ethyl acetate (x3). The combined organic extracts were then washed with brine and dried (Na2SC^) to provide the crude (R)-2-(5-Bromo- thiophene-2-sulfonylamino)-3-(lH-indol-3-yl)-propionic acid product (3) (O.lg, 74 %). LC-MS (ES+) 429, 431; (ES-) 427, 429.A portion of the crude (R)- 2-(5-Bromo-thiophene-2-sulfonylamino)-3-(lH-indol-3-yl)- propionic acid product (3) was taken to the next step without further purification.

153-94-6, The synthetic route of 153-94-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AQUILUS PHARMACEUTICALS, INC; SUCHOLEIKI, Irving; WO2010/75287; (2010); A2;,
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

General procedure: A solution of compounds (1.5 mg) in 6 M HCl (1 ml) was heated to 120 C for 24 h. The solution was then evaporated to dryness and the residue redissolved in H2O (100 mul) and was then placed in a 1 ml reaction vial and treated with a 2% solution of FDAA (200 mul) in acetone followed by 1.0 M NaHCO3 (40 mul). The reaction mixture was heated at 47 C for 1 h, cooled to room temperature, and then acidified with 2.0 M HCl (20 mul). In a similar fashion, standard D- and L-amino acids were derivatized separately. The derivatives of the hydrolysates and standard amino acids were subjected to analytical HPLC analysis (Shimadzu LC-20AD, C18 column; 5 mum, 4.6 mm ¡Á 250 mm; 1.0 ml/min) at 30 C using the following gradient program: solvent A, water + 0.2% TFA; solvent B, MeCN; linear gradient 0 min 25% B, 40 min 60% B, 45 min 100% B; UV detection at 340 nm [39]., 153-94-6

As the paragraph descriping shows that 153-94-6 is playing an increasingly important role.

Reference£º
Article; Nishanth Kumar; Mohandas; Nambisan, Bala; Peptides; vol. 53; (2014); p. 48 – 58;,
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

D-Tryptophan (100 g), and PTSA.H20 (186.28 g) were added to allyl alcohol (1000 ml) stirred at 25 to 35C, followed by addition of toluene (500ml). The resulting mixture was stirred at 80-95C till completion of reaction, as monitored by TLC. After completion, the mass was cooled, and 5% aqueous sodium bicarbonate solution was added to it. Extraction with ethyl acetate followed by separation and concentration of the organic layer gave a residue containing H-D-Trp-OAll (11). Yield: 108.01 g (90.3%) Purity: > 95% (HPLC)

153-94-6, As the paragraph descriping shows that 153-94-6 is playing an increasingly important role.

Reference£º
Patent; EMCURE PHARMACEUTICALS LIMITED; GURJAR, Mukund Keshav; TRIPATHY, Narendra Kumar; PRAMANIK, Chinmoy Mriganka; DESHPANDE, Ashish Pramod; (25 pag.)WO2017/178950; (2017); A1;,
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

Synthesis of methyl esters of L- and D-tryptophanes chlorohydrates; :1a,b 2a,b a : D b : L[0344] Thionylchloride (0.064 mol) was slowly added to a cooled (O0C) suspension of tryptophane (0.049 mol) in methanol (150 mL). The reaction mixture was warmed up to 4O0C and stirred at this temperature for six hours. All solvents were removed and the solid residue was triturated with ether. The solid was filtered off to give the required product.[0345] D-tryptophane (2a): yield 98 %, M.p. 232-233C. NMR1H (delta, ppm,DMSO-dtheta, 300 MHz): 3.39 (2H, m, CH2); 3.63 (3H, s, CH3O); 4.20 (1 H1 t, CH, JHH = 5.5 Hz); 7.07 (2H, dt, Ar, JHH = 21 Hz, 6 Hz); 7.26 (1 H, d, H2, JHH = 3 Hz); 7.39 (1 H, d, Ar, JHH = 7.8 Hz); 7.53 (1 H, d, Ar, JHH = 7.8 Hz). NMR13C (delta, ppm, DMSO-d6, 125.76 MHz): 26.01 (s), 52.61 (d), 106.26(s), 111.45(s), 117.84(s), 118.50(s), 121.05(s), 124.80(s), 126.79(s), 136.13(s), 169.57(s). m/z 218(M+)., 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; TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; WO2008/103470; (2008); A2;,
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

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

C1. D-Tryptophan methyl ester; The title compound can be obtained by methylesterification of D-tryptophan in methanol with the aid of thionylchloride according to standard procedures., 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; ALTANA PHARMA AG; WO2006/79645; (2006); 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.153-94-6,H-D-Trp-OH,as a common compound, the synthetic route is as follows.

Example 1 To a 1L three-necked flask was added 200mL of tetrahydrofuran, 20g D-tryptophan, 7.7g methylaminoacetonitrile, 38.2g EDC ¡¤ HCl and 1g 4-dimethylaminopyridine. The reaction was stirred at room temperature for 5 hours. After completion of the reaction, 300mL of ethyl acetate and 300mL water was added. The ethyl acetate layer was washed with 200mL saturated sodium chloride and stirred. Still stratification of the ethyl acetate layer was distilled under reduced pressure at 30C to a volume of about 200ml. The solution was recrystallized with 700ml of petroleum ether, filtered and vacuum dried at 40C to give 22.25g of compound III. HPLC purity 98%, Yield 91%., 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; Zhejiang Yongning Pharmaceutical Co., Ltd.; Ye, Tianjian; Yuan, Youting; Chen, Xin; Zhang, Hongxun; (7 pag.)CN105348283; (2016); A;,
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

Thionyl chloride (9.87 mmol, 0.72 mL) was added dropwise to a solution of D-tryptophan (1.000 g, 4.89 mmol) in methanol (33 mL). The reaction was heated to reflux with vigorous stirring for 24 h. After cooling, the reaction mixture was concentrated under reduced pressure and residual methanol traces removed by azeotropic distillation with dichloromethane (10 mL) under reduced pressure to give the title compound as a white solid (1.070 g, 86%). [0401] 1H NMR (500 MHz, D2O) delta=7.52 (1H, d, J=7.9, 9-H), 7.46 (1H, d, J=8.1, 12-H), 7.26-7.10 (3H, m, 4, 5, 9-H), 4.37 (1H, t, J=6.0, 2-H), 3.73 (3H, s, beta-H), 3.44-3.31 (2H, m, 4-H). [0402] 13C NMR (126 MHz, D2O) delta=170.4 (2-C), 136.3 (7-C), 126.4 (8-C), 125.4 (6-C), 122.3 (11-CH), 119.6 (10-CH), 118.1 (9-CH), 112.1 (12-CH), 106.0 (5-C), 53.6 (13-CH3), 53.3 (2-CH), 25.7 (4-CH2). [0403] IR (diamond, vMAX, cm-1) 3261 (NH st), 2870 (N+-H st), 2023 (Ar comb), 1748 (C?O st), 1229, 1211 (CO-O st as), 1181 (C-O st as). [0404] Acc. Mass (FAB): C12H15N2O2 Found: 219.1120 m/z Calculated: 219.1128 m/z., 153-94-6

The synthetic route of 153-94-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The University of Sussex; Viseux, Eddy Michel Elie; Gallop, Christopher; Bobin, Mariusz; US2014/39200; (2014); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI