Synthesis of N-Cbz Amides and Their Applications in the Transamidation Reactions at Room Temperature

Abstract

A wide range of aryl and alkyl N-Cbz amides were prepared from secondary amides and benzyl chloroformate in the presence of LiHMDS. Application of N-Cbz amides in transamidation was demonstrated with different amines at room temperature in the presence of DBU. The reactivity of N-Cbz amides is comparable with N-Boc and N-Ts amides in transamidation and transesterification reactions. The optimized condition was well-suited for the transesterification reactions with thiols and alcohols. Broad substrate scope and excellent yields are the merits of the developed methodology. © 2022 Wiley-VCH GmbH.