Development of a Suitable Process for the Preparation of a TNF-α Converting Enzyme Inhibitor, WAY-281418

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• 作者：Youchu Wang ; Maria Papamichelakis ; Warren Chew ; John Sellstedt ; Razzak Noureldin ; Sam Tadayon ; Sylvain Daigneault ; Rocco J. Galante ; Jerry Sun
• 刊名：Organic Process Research & Development
• 出版年：2008
• 出版时间：November 21, 2008
• 年：2008
• 卷：12
• 期：6
• 页码：1253-1260
• 全文大小：216K
• 年卷期：v.12,no.6(November 21, 2008)
• ISSN：1520-586X

文摘

A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydrogenation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.