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【结 构 式】

【分子编号】68253

【品名】(2S,4R)-tert-butyl 4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-2-(((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidine-1-carboxylate

【CA登记号】 

【 分 子 式 】C29H35ClN4O8S

【 分 子 量 】635.138

【元素组成】C 54.84% H 5.55% Cl 5.58% N 8.82% O 20.15% S 5.05%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXV)

Alternatively, condensation of 1,7-dichloro-4-methoxyisoquinoline (XXI) with 1-(tert-butoxycarbonyl)-4(R)-hydroxy-L-proline (XVI) in the presence of t-BuOK in DMSO gives 1-(tert-butoxycarbonyl)-4(R)-[(7-chloro-4-methoxyisoquinolin-1-yl)oxy]-L-proline (XXIV), which is then coupled with 1(R)-amino-2(S)-vinylcyclopropanecarboxamide (XI) by means of EDC, HOBt and DIEA , or HATU and DIEA in CH2Cl2 , to yield the corresponding dipeptide derivative (XXV). NBoc cleavage by means of HCl in i-PrOH (1) or refluxing MeOH provides amine hydrochloride (XXVI), which is finally condensed with N-(tert-butoxycarbonyl)-3-methyl-L-valine (XIX) using HATU and DIEA in .

1 Perrone, R.K., Wang, C., Ying, W., Song, A.I. (Bristol-Myers Squibb Co.).Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-cholor-4-methoxy-1-isoquino linyl)oxy)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide. CN 101903371, EP 2231639, JP 2011507869, KR 2010099703, WO 2009085659.
2 Sun, L.Q., Wang, A.X., Chen, J. et al. Design and optimization of a series of potent and novel HCV NS3 protease inhibitors leading to the discovery of BMS-650032. 241st ACS Natl Meet (March 27-30, Anaheim) 2011, Abst MEDI 73.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 68243 tert-butyl ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamate hydrochloride   C14H22N2O5S.HCl 详情 详情
(XVI) 16094 (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;1-(tert-butoxycarbonyl)-4®-hydroxy-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid 16094 C10H17NO5 详情 详情
(XIX) 22251 (2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutyric acid;2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid;N-(tert-butoxycarbonyl)-3-methyl-L-valine 62965-35-9 C11H21NO4 详情 详情
(XXI) 68249 1,7-dichloro-4-methoxyisoquinoline   C10H7Cl2NO 详情 详情
(XXIV) 68254 1-(tert-butoxycarbonyl)-4(R)-[(7-chloro-4-methoxyisoquinolin-1-yl)oxy]-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid   C20H23ClN2O6 详情 详情
(XXV) 68253 (2S,4R)-tert-butyl 4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-2-(((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidine-1-carboxylate   C29H35ClN4O8S 详情 详情
(XXVI) 68252 (2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-N-((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)pyrrolidine-2-carboxamide hydrochloride   C24H27ClN4O6S.HCl 详情 详情
Extended Information