Multi-Kiloscale Enantioselective Synthesis of a Vitronectin Receptor Antagonist

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• 作者：Michael D. Wallace ; Michael A. McGuire ; Marvin S. Yu ; Lynn Goldfinger ; Li Liu ; Wenning Dai ; and Susan Shilcrat
• 刊名：Organic Process Research & Development
• 出版年：2004
• 出版时间：September 2004
• 年：2004
• 卷：8
• 期：5
• 页码：738 - 743
• 全文大小：107K
• 年卷期：v.8,no.5(September 2004)
• ISSN：1520-586X

文摘

The development of a novel, cost-effective synthesis of thevitronectin receptor antagonist SB-273005 became necessaryas the compound proceeded to Phase 1. A practical synthesisof the compound presented challenges to the process chemist.Chief among the challenges was developing an enantioselectiveroute to the compound. Second was either developing a scalableMitsunobu coupling of the side chain to the main body orfinding alternate chemistry. In this paper we will describe thechemistry we developed which allowed us to make over ahundred kilograms of SB-273005 by a process that we believeis suitable for even larger scale manufacturing.