Tetrahedron

Deprotection of t-butyl esters of amino acid derivatives by nitric acid in dichloromethane

P Strazzolini, M Scuccato, AG Giumanini

Index: Strazzolini, Paolo; Scuccato, Massimo; Giumanini, Angelo G. Tetrahedron, 2000 , vol. 56, # 22 p. 3625 - 3633

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Citation Number: 25

Abstract

The extension of the deprotection procedure of t-butylated carboxyl function using HNO3 in CH2Cl2 to a number of appropriately selected NZ-derivatives of natural amino acid esters was investigated. The method was found to work effectively with alanine, phenylalanine, serine and the dipeptide aspartame, but the reagent brought about a number of unwanted transformations with tyrosine, methionine and tryptophan. Suitable protection of functions ...