New methods of introducing the carbo-tert-butoxy amino-protecting group. tert-Alkyl chloroformates substituted with electron-withdrawing substituents

LA Carpino, KN Parameswaran…

Index: Carpino,L.A. et al. Journal of Organic Chemistry, 1970 , vol. 35, p. 3291 - 3295

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Citation Number: 31

Abstract

1970 a-Bromo-and a, a-dibromo-t-butyl chloroformate have been synthesized and found to be significantly more stable than t-butyl chloroformate. On treatment with aniline and other amines the corresponding urethans were obtained although the acylation reaction was generally unsuccessful with amino acid derivatives. Catalytic reduction of the carbanilates over a palladium-carbon catalyst gave the corresponding carbo-t-butoxy derivatives ...