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.