Organic Chemistry Portal

Abstracts

Search:

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

Joshua R. Dunetz, Yanqiao Xiang, Aaron Baldwin and Justin Ringling

*Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States, Email: joshua.r.dunetzpfizer.com

J. R. Dunetz, Y. Xiang, A. Baldwin, J. Ringling, Org. Lett., 2011, 13, 5048-5051.

DOI: 10.1021/ol201875q (free Supporting Information)


Abstract

The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine enables a low-epimerization amide bond formation. This robust and practical 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.

see article for more examples



Key Words

amides


ID: J54-Y2011-2820