Use of silyl ester and enamine protection for an efficient alternate synthesis of (1S,2S,5R,6S)-2-[(2′S)-(2′-amino)propionyl]aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid hydrochloride (LY544344•HCl)

被引：4

作者：

Fennell, Jared W. ^{[1
]}

Semo, Michael J.

Wirth, David D.

Vaid, Radhe K.

机构：

[1] Chem Prod Res & Dev, Lafayette, IN 47902 USA

[2] Eli Lilly & Co, Tippecanoe Labs, Lafayette, IN 47902 USA

来源：

SYNTHESIS-STUTTGART | 2006年 / 16期

关键词：

acylations; protecting groups; amino acids; drugs; process development;

D O I：

10.1055/s-2006-942487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An alternate synthesis of title compound (5) using Ar-(2-methoxycarbonyl-l-methylvinyl)-L-alanine sodium salt (6) and 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (1) was successfully completed. Incorporation of silyl ester protection and the use of an enamine-protecting group allowed for the elimination of several processing steps.

引用

页码：2659 / 2664

页数：6

共 12 条

[1]

BARTON JW, 1973, PROTECTIVE GROUPS OR, P67

[2] MOLECULAR STRUCTURAL REQUIREMENTS FOR BINDING AND ACTIVATION OF L-ALANINE TASTE RECEPTORS [J].