Category: 137076-54-1

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137076-54-1,2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid,as a common compound, the synthetic route is as follows.

Example 2 (S)-2,2′-bis[bis(3,5-dimethylphenyl)phosphino]-1,1′-binaphthyl Under an argon atmosphere, to a solution (5 ML) of [1,2-bis(diphenylphosphino)-ethane]dichloronickel (42 mg, 0.1 equivalent), (S)-2,2′-bis(trifluoromethanesulfonyloxy)-1,1′-binaphthyl (399 mg, 0.73 MmoL) synthesised in Reference Example 1 and 1,4-diazabicyclo[2,2,2]octane (489 mg, 6.0 equivalents) in DMF was added at room temperature a bis(3,5-dimethylphenyl)phosphine-borane complex (428 mg, 2.3 equivalents) synthesised in Example 1.. The mixture was stirred at room temperature for 30 min. and then at 110C for 96 hrs. DMF was evaporated under reduced pressure and methanol was added to the residue to give the title compound (329 mg, pale-yellow white crystals).. yield 62%.1H-NMR (300 MHz, CDCl3, TMS) delta: 2.06 (s, 12H), 2.13 (s, 12H), 6.70-6.73 (m, 10H), 6.81 (s, 2H), 6.90 (d, 2H, J = 8.46 Hz), 7.01 (dd, 2H, J = 7.14Hz, 7.14Hz), 7.39 (dd, 2H, J = 6.99Hz, 6.99Hz), 7.52 (dd, 2H, J = 8.49Hz, 2.28Hz), 7.84-7.88 (m, 4H).31P-NMR (121 MHz, CDCl3, 85%H3PO4) delta: -14.25 (s). (ref.: 31P-NMR (161 MHz, CDCl3, 85%H3PO4) delta: -14.9.. Journal of Organic Chemistry, vol. 59, p. 3064 (1994)

137076-54-1, The synthetic route of 137076-54-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; EP1452537; (2004); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

137076-54-1, 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The procedure that was followed was described in Li, C, et al., J. Am. Chem. Soc, 2006, 128, 15072-73. Compound 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid (400 mg, 0.70 mmol), N-hydroxysuccinimide (90.4 mg, 0.78 mmol, 1.1 equiv.), and O-benzotriazol-1-yl-N,N,N’,N-tetramethyluronium hexafluorophosphate (HBTU) (296 mg, 0.78 mmol, 1.1 equiv.) were dissolved in 10 mL of acetonitrile. The reaction was stirred at room temperature for 24 hr. After removing the solvent under vaccum, the crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 85:15) to give compound tri-tert-butyl 2,2′,2″-(10-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate as a white foam (404 mg, 86 %) Rf : 0.3 (CH2Cl2/MeOH, 85:15). 1H NMR (300MHz, CDCl3) delta 3.51 (br, 4H, H8), 3.54 (br, 4H, H13, H1′), 3.32-3.26 (m, 4H, H6), 3.08-2.99 (m, 4H, H5), 2.97-2.86 (m, 8H, H2, H3), 2.85 (s, H4′), 1.46 (s, 18H, H12), 1 .45 (s, 9H, H17). 13C NMR (75MHz, CDCl3) delta 173.4 (C9, C14), 173.1 (C2′), 169.9 (C3′), 82.6 (C16), 82.4 (C11), 55.8 (C8), 55.7 (C13), 54.2 (C1′), 54.1 -51 .5 (C2, C3), 51 .0-48.9 (C5, C6), 27.8 (C17), 27.6 (C12). 25.6 (C4′) MS (CI/NH3) m/z 692 [M + H]+

The synthetic route of 137076-54-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INSTITUT CURIE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE PIERRE ET MARIE CURIE (PARIS 6); FLORENT, Jean-Claude; AIT SARKOUH, Rafik; JOHANNES, Ludger; SCHMIDT, Frederic; OBERLEITNER, Birgit; DRANSART, Estelle; SEMETEY, Vincent; WO2014/86942; (2014); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

137076-54-1, 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DOTA(tBu)3-OH (100 mg, 0.175 mmol, 1.0 eq.) was dissolved in dry DMF (0.5 ml), HATU (66.4 mg, 0.175 mmol, 1.0 eq.) dissolved in dry DMF (0.5 ml) and Collidine (46.1 mu, 0.350 mmol, 2.0 eq.) were added. After 5 min this mixture was slowly added to a 0C cold solution of ethylendiamine (0.873 mmol. 5.0 eq.) in dry DMF (1.5 ml). After stirring for 19 h DMF was evaporated, the residual oil was dissolved in EtOAc (5 ml) and extracted with water (0.5 ml), sat. aq. NaHC03 (0.5 ml) and sat. aq. NaCl (0.5 ml). The organic layer was dried over Na2S04, evaporated and the resiude was purified by flash chromatography with DCM, DCM/methanol 20/1 and DCM/methanol 10/1 as eluents. This yielded 45 mg of mono- acylated ethylendiamine. A solution of this material (18 mg, 29 mupiiotaomicron) in dry DMF (0.2 ml) was added to a 10 min preactivated solution of SR- 142948 (20 mg, 29 mupiiotaomicron) [HATU (11.1 mg, 29 muetaiotaomicron) and DIPEA (10 mu, 58 muetaiotaomicron, 2eq.) in dry DMF (0.4 ml)]. After 15 h monoacylated ethylendiamine (9 mg, 15muiotaetaomicron1, 0.5 eq.) in dry DMF (0.1 ml) was added. 5 h later the reaction mixture was heated to 60C for 30 min. Then the solvents were evaporated and the material purified by prep. HPLC (15 to 55% B in 30 min, Agilent PLRP-S 25 x 150 mm). This yielded the title compound of formula (XVIII) (15 mg, 12mupiiotaomicron1, 40%). HPLC: Rt = 3.9 min. MS: m/z = 1282.7 ([M+H]+, calculated 1282.8) (MW = 1282.65).

The synthetic route of 137076-54-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; 3B PHARMACEUTICALS GMBH; OSTERKAMP, Frank; SMERLING, Christiane; REINEKE, Ulrich; HAASE, Christian; UNGEWIss, Jan; WO2014/86499; (2014); 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.137076-54-1,2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid,as a common compound, the synthetic route is as follows.

(1)To a solution of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetate tri-tert-butyl (24.8 mg), DMF (0.2 mL) and DIEA (17 muL) was added HBTU (17.0 mg) in DMF (100 muL), and then added to a solution of (L 7) (13.1 mg) in DMF (200 muL) and DIEA (10 muL) and stirred at room temperature for 1 hour. Water (200 muL) was added and purified by preparative HPLC to give (M 1) (12.3 mg).

137076-54-1 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid 11606627, acatalyst-ligand compound, is more and more widely used in various.

Reference£º
Patent; FUJIFILM Corporation; Fujifilm RI Pharma Co., Ltd.; Hirofumi, Fukunaga; Do En, Hiroyuki; Hino, Akihiro; Oshikiri, Shinobu; Chou, Rumpf; (131 pag.)JP2016/183151; (2016); A;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

137076-54-1, 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(7) To a solution of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetate (5.9 mg) and compound (Z6) (6.7 mg) in NMP (200 muL) and DIEA (20 muL), HBTU (5.2 mg) was added, and the mixture was stirred at room temperature for 50 minutes. Methanol (100 muL) was added thereto, and then, the mixture was purified by preparative HPLC to obtain compound (Z7) (3.9 mg). LC/MS (ACQUITY) rt (min): 1.08 MS (ESI, m/z): 763.9 [M+2H]2+

137076-54-1 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid 11606627, acatalyst-ligand compound, is more and more widely used in various.

Reference£º
Patent; FUJIFILM Corporation; FUJIFILM RI PHARMA CO., LTD.; FUKUNAGA, Hirofumi; DOZONO, Hiroyuki; HINO, Akihiro; OSHIKIRI, Shinobu; NAGANO, Akio; (99 pag.)US2016/199520; (2016); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

137076-54-1, 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The product of Part 17B (131 mg, 0.250 mmol) was dissolved in 2:1 MeCN/H2O (5.00 mL) and successively treated with 14.2 mg TPPTS (25.0 mumol; 10 mol %), Et2NH (129 muL, 1.25 mmol) and 2.8 mg Pd(OAc)2 (12.5 mumol; 5 mol %) at 22 C. Complete deprotection was observed within 0.25 h. The resulting amber solution was then lyophilized to remove all volatile components. The solids thus obtained were redissolved in DMF and successively treated with HOBt (45.9 mg, 0.300 mmol), 2-(1,4,7,10-tetraaza-4,7,10-tris{[(tert-butyl)oxycarbonyl]methyl}-cyclododecyl)acetic acid (172 mg, 0.300 mmol), i-Pr2NEt (105 muL, 0.600 mmol) and HBTU (114 mg, 0.300 mmol) at 22 C. After 0.25 h, complete acylation was observed; only trace amounts of regioisomeric and dimeric products formed. The resulting solution was partitioned between EtOAc and H2O (50 mL each) with transfer to a separatory funnel. The layers separated and the aqueous layer washed with EtOAc (2¡Á50 mL). The EtOAc solution was further washed with 0.1 M NaOH (3¡Á50 mL) and saturated aqueous NaCl (3¡Á50 mL each), then dried over MgSO4, filtered and concentrated in vacuo to a pale yellow oil that was used without further purification in the subsequent deprotection step. The protected conjugate (0.250 mmol theoretical) was dissolved in dioxane (2.50 mL) then successively treated with H2O (23 muL) and HCl (10.0 mmol; 2.50 mL of a 4 M solution in dioxane) at 22 C. The resulting pale yellow solution was stirred 17 h, during which time a heavy white precipitate formed. Upon complete deprotection, the volatiles were removed under a stream of N2 and the white solid residue redissolved in H2O containing 0.1% TFA (8.00 mL) then partially purified by HPLC on a Phenomenex Luna C18 column (21.2¡Á250 mm) using a 2%/min gradient from 0-60% MeCN containing 0.1% TFA and 10% H2O at 20 mL/min. The main product peak eluting at 21 min was collected and lyophilized to a white powder. Final purification was performed using the identical column and method. The main product peak was collected and lyophilized to a white powder (0.110 g, 97.3 mumol; 38.9%).

As the paragraph descriping shows that 137076-54-1 is playing an increasingly important role.

Reference£º
Patent; Lantheus Medical Imaging, Inc.; Cesati, Richard R.; Harris, Thomas D.; Robinson, Simon P.; Looby, Richard J.; Cheesman, Edward H.; Yalamanchili, Padmaja; Casebier, David S.; (86 pag.)US9266846; (2016); B2;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

137076-54-1, 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 2-(1,4,7,10-tetraaza-4,7,10-tris{[(tert-butyl)oxycarbonyl]methyl}-cyclododecyl)acetic acid (68.7 mg, 0.120 mmol) in dry DMF (1.00 mL) was successively treated with HOBt (18.4 mg, 0.120 mmol) and EDC (22.9 mg, 0.120 mmol) at 22 C. After 0.5 h, the solution was treated with the product of Part 18A (40.8 mg, 0.100 mmol) and the resulting mixture stirred 0.5 h. The intermediate conjugate thus obtained was once again activated with EDC (22.9 mg, 0.120 mmol), then stirred 0.5 h before final treatment with MeONH2.HCl (10.0 mg, 0.120 mmol). After 1 h, the resulting mixture was diluted with EtOAc (100 mL) then transferred to a separatory funnel and successively washed with 0.1 M NaOH and saturated aqueous NaCl (3¡Á25 mL each). The EtOAc solution was dried over MgSO4, filtered and concentrated in vacuo to a colorless oil, which was used without further purification in the subsequent deprotection step.The protected conjugate (0.120 mmol theoretical) was dissolved in dioxane (1.00 mL) then successively treated with H2O (9 muL) and HCl (4.00 mmol; 1.00 mL of a 4 M solution in dioxane) at 22 C. The resulting pale yellow solution was stirred 14 h, during which time a heavy white precipitate formed. Upon complete deprotection, the volatiles were removed under a stream of N2 and the white solid residue redissolved in H2O containing 0.1% TFA (8.00 mL) then directly purified by HPLC on a Phenomenex Luna C18 column (21.2¡Á250 mm) using a 1%/min gradient from 0-30% MeCN containing 0.1% TFA and 10% H2O at 20 mL/min. The main product peak eluting at 11.5 min was collected and lyophilized to a white powder (12.8 mg, 13.4 mumol; 13.4%).

137076-54-1 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid 11606627, acatalyst-ligand compound, is more and more widely used in various.

Reference£º
Patent; Lantheus Medical Imaging, Inc.; Cesati, Richard R.; Harris, Thomas D.; Robinson, Simon P.; Looby, Richard J.; Cheesman, Edward H.; Yalamanchili, Padmaja; Casebier, David S.; (86 pag.)US9266846; (2016); B2;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI