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【结 构 式】

【分子编号】68247

【品名】(2S,4R)-N-((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-hydroxypyrrolidine-2-carboxamide 2,2,2-trifluoroacetate

【CA登记号】 

【 分 子 式 】C14H21N3O5S.C2HF3O2

【 分 子 量 】457.428

【元素组成】C 42.01% H 4.85% F 12.46% N 9.19% O 24.48% S 7.01%

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:(XVIII)

Coupling of primary amine (XI) with 1-(tert-butoxycarbonyl)-4(R)-hydroxy-L-proline (XVI) by means of HATU and DIEA in CH2Cl2 gives dipeptide (XVII), which is treated with TFA in CH2Cl2 to provide the deprotected dipeptide (XVIII). Condensation of peptide (XVIII) with N-(tert-butoxycarbonyl)-3-methyl-L-valine (XIX) using HATU and DIEA in CH2Cl2 affords tripeptide (XX), which is finally condensed with 1,7-dichloro-4-methoxyisoquinoline (XXI) in the presence of LaCl3 and t-BuOK in DMF (1).
1,7-Dichloro-4-methoxyisoquinoline (XXI) is obtained by cyclization of 3-(4-chlorophenyl)-3-methoxyacrylic acid (XXII) with (PhO)2PON3 by means of of Et3N in benzene, resulting in 7-chloro-4-methoxyisoquinolin-1(2H)-one (XXIII), which is then chlorinated with POCl3 in refluxing DMF .

1 Campbell, J.A., Wang, X.A., Sin, N. et al. (Bristol-Myers Squibb Co.). Hepatitis C virus inhibitors. EP 1505963, EP 2340830, JP 2005533028, KR 2010093140, US 200410659, US 6995174, US 2011311482, WO 200309974.
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
(XVII) 68248 (2S,4R)-tert-butyl 2-(((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidine-1-carboxylate   C19H29N3O7S 详情 详情
(XVIII) 68247 (2S,4R)-N-((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-hydroxypyrrolidine-2-carboxamide 2,2,2-trifluoroacetate   C14H21N3O5S.C2HF3O2 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
(XX) 68246 tert-butyl (1-((2S,4R)-2-(((1S,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate   C25H40N4O8S 详情 详情
(XXI) 68249 1,7-dichloro-4-methoxyisoquinoline   C10H7Cl2NO 详情 详情
(XXII) 68250 3-(4-chlorophenyl)-3-methoxyacrylic acid   C10H9ClO3 详情 详情
(XXIII) 68251 7-chloro-4-methoxyisoquinolin-1(2H)-one   C10H8ClNO2 详情 详情
Extended Information