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.
Synthesis of various glycouronamides via transamidation reaction is reported under mild reaction conditions. Transamidation of N-nitroso uronamides with primary and secondary amines was successfully achieved in the presence of triethyl amine. On the other hand, N-Boc uronamides underwent transamidation smoothly with various primary amines in the presence of DBU. These reactions provided the desired glycouroamides in good to excellent yields at room temperature.
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