Selective tert-butyl ester deprotection in the presence of acid labile protecting groups with use of ZnBr2

The Journal of Organic Chemistry
Ramesh KaulWilliam D Lubell

Abstract

Chemoselective hydrolysis of tert-butyl esters in the presence of other acid-labile groups has been explored by employing alpha-amino esters and ZnBr(2) in DCM. Although N-Boc and N-trityl groups were found to be labile, PhF protected amines were compatible with these Lewis acid deprotection conditions such that a variety of N-(PhF)amino acids were prepared in good yields from their corresponding tert-butyl esters.

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