Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

被引：25

作者：

Brands, KMJ

Jobson, RB

Conrad, KM

Williams, JM

Pipik, B

Cameron, M

Davies, AJ

Houghton, PG

Ashwood, MS

Cottrell, IF

Reamer, RA

Kennedy, DJ

Dolling, UH

Reider, PJ

机构：

[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

[2] Merck Sharp & Dohme Ltd, Dept Proc Res, Hoddesdon EN11 9BU, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 14期

关键词：

D O I：

10.1021/jo011170c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3- [[(4-mercapto-2-pyrrolidinyl)carbonyl] amino] benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

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收藏

页码：4771 / 4776

页数：6

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