Process development on an efficient new convergent formal synthesis of MIV-150

被引：18

作者：

Cai, SP ^{[1
]}

Dimitroff, M ^{[1
]}

McKennon, T ^{[1
]}

Reider, M ^{[1
]}

Robarge, L ^{[1
]}

Ryckman, D ^{[1
]}

Shang, X ^{[1
]}

Therrien, J ^{[1
]}

机构：

[1] Chiron Corp, Chem Dev Dept, Seattle, WA 98119 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2004年 / 8卷 / 03期

关键词：

D O I：

10.1021/op0341871

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Starting from a known linear route and a proposed convergent route, we have successfully developed a new hybrid convergent route to MIV-150 that takes advantage of the robust chemistry for the preparation of a fluoroketal and the stereospecific Negishi coupling of an iodocyclopropane moiety to a benzene ring. Stereoselective beta- and cis-iodination chemistry was developed for the preparation of an enantiomerically pure iodocyclopropanecarboxylate. Following the Negishi coupling, proven chemistry from the linear route was incorporated, thus ensuring a similar high-purity profile for the final active pharmaceutical ingredient (API). In addition, we have prepared and evaluated a series of basic inorganic and organic MIV-150 salts that have drastically increased water solubility over the parent compound.

引用

页码：353 / 359

页数：7

共 18 条

[1]

ASHRAF B, 2003, ORG BIOMOL CHEM, V1, P5

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