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【结 构 式】

【分子编号】60439

【品名】(1S,2S,3R,4R)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]pyrrolidinyl}carbonyl)amino]bicyclo[2.2.1]heptane-2-carboxylic acid

【CA登记号】

【 分 子 式 】C19H22Cl2N2O5S

【 分 子 量 】461.36556

【元素组成】C 49.46% H 4.81% Cl 15.37% N 6.07% O 17.34% S 6.95%

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:(VIII)

Acylation of L-proline t-butyl ester (I) with 3,5-dichlorobenzenesulfonyl chloride (II) affords sulfonamide (III). The tert-butyl ester group of (III) is then cleaved by treatment with aqueous trifluoroacetic acid, yielding carboxylic acid (IV). Coupling of sulfonyl proline (IV) with the racemic 3-endo-amino-bicyclo[2.2.1]heptane-2-endo-carboxylate (V) leads to a mixture of four diastereoisomeric amides, resulting from carboxylate group epimerization. This mixture can be separated into two pairs of diastereoisomers (VI) and (VII) by flash chromatography. The desired diastereoisomeric mixture of esters (VII) is then hydrolyzed under alkaline conditions to furnish the title carboxylic acid along with its epimer (VIII).

1 Chang, L.L.; Truong, Q.; Doss, G.; et al.; Orally active, conformationally constrained small molecule VLA-4 antagonists. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 325.
2 Hagmann, W.K.; MacCoss, M.; Chang, L. (Merck & Co., Inc.); Cyclic amino acid derivs. as cell adhesion inhibitors. JP 2001523711; US 6271252; WO 9926615 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
rac-(V) 60436 ethyl (1S,2S,3R,4R)-3-aminobicyclo[2.2.1]heptane-2-carboxylate C10H17NO2 详情 详情
(I) 19832 tert-butyl (2S)-2-pyrrolidinecarboxylate C9H17NO2 详情 详情
(II) 59023 3,5-dichlorobenzenesulfonyl chloride C6H3Cl3O2S 详情 详情
(III) 60434 tert-butyl (2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-pyrrolidinecarboxylate C15H19Cl2NO4S 详情 详情
(IV) 60435 (2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-pyrrolidinecarboxylic acid C11H11Cl2NO4S 详情 详情
(VI) 60437 ethyl (1R,3S,4S)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]pyrrolidinyl}carbonyl)amino]bicyclo[2.2.1]heptane-2-carboxylate C21H26Cl2N2O5S 详情 详情
(VII) 60438 ethyl (1S,3R,4R)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]pyrrolidinyl}carbonyl)amino]bicyclo[2.2.1]heptane-2-carboxylate C21H26Cl2N2O5S 详情 详情
(VIII) 60439 (1S,2S,3R,4R)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]pyrrolidinyl}carbonyl)amino]bicyclo[2.2.1]heptane-2-carboxylic acid C19H22Cl2N2O5S 详情 详情
Extended Information