Acylation of N-Boc-N’-COCF3 protected hydrazine
Date
2024
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
Tartu Ülikool
Abstract
Within the scope of the present thesis acylation of N-Boc-N’-COCF3 protected hydrazine was
investigated. Acetic anhydride, benzoyl and butanoyl chlorides, activated esters and benzyl
chloroformate were tested as acylating agents. The implementation of highly reactive acyl
chlorides led to very good yields of hydrazines monoacylated at the Boc-protected nitrogen.
Application of an excess of acyl chlorides promoted the formation of diacylated Boc-protected
hydrazines and an unexpected loss of the trifluoroacetic group. Acylation by
activated esters or benzyl chloroformate resulted solely in monoacylated products isolated in
fair to poor yields. Reactions utilizing acetic anhydride gave no product irrespective of
reaction conditions.
Description
Keywords
Hydrazine, Acylation, Orthogonal protecting groups