Development of a Practical and Convergent Process for the Preparation of Sulopenem

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• 作者：Steven J. Brenek ; St茅phane Caron ; Esmort Chisowa ; Mark P. Delude ; Michele T. Drexler ; Marcus D. Ewing ; Robert E. Handfield ; Nathan D. Ide ; Durgesh V. Nadkarni ; Jade D. Nelson ; Mark Olivier ; Hahdi H. Perfect ; James E. Phillips ; John J. Teixeira ; R. Matt Weekly ; John P. Zelina
• 刊名：Organic Process Research & Development
• 出版年：2012
• 出版时间：August 17, 2012
• 年：2012
• 卷：16
• 期：8
• 页码：1348-1359
• 全文大小：595K
• 年卷期：v.16,no.8(August 17, 2012)
• ISSN：1520-586X

文摘

Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.