General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine

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• 作者：Joshua R. Dunetz ; Yanqiao Xiang ; Aaron Baldwin ; Justin Ringling
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：October 7, 2011
• 年：2011
• 卷：13
• 期：19
• 页码：5048-5051
• 全文大小：800K
• 年卷期：v.13,no.19(October 7, 2011)
• ISSN：1523-7052

文摘

The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.