A Scalable Oxidation for the Final Stage of Synthesis of Cathepsin K Inhibitor SB-462795

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• 作者：Steven N. Goodman ; Qunying Dai ; Jun Wang ; William M. Clark ; Jr.
• 刊名：Organic Process Research & Development
• 出版年：2011
• 出版时间：January 21, 2011
• 年：2011
• 卷：15
• 期：1
• 页码：123-130
• 全文大小：375K
• 年卷期：v.15,no.1(January 21, 2011)
• ISSN：1520-586X

文摘

In developing the manufacturing route for the cathepsin K inhibitor SB-462795, the oxidation of a secondary alcohol for the final chemical stage is described. Prospective conditions were limited by several factors, particularly general safety concerns of oxidation reactions, the requirement to control impurities and transition metals isolated in the final product, and the desire to reduce the environmental impact. Two N-oxy free radical approaches (TEMPO and PIPO) and Moffatt conditions were evaluated in depth for their potential to achieve the targets. For reasons of robustness, scalability, and cost-effectiveness, the Moffatt conditions were the best manufacturing option.