Reactivities of trimethylsilyl derivatives of amino acids in aminolysis of activated esters

Abstract

1. A study has been made of the activity of the amino-acid alkyl esters and their N-trimethylsilyl derivatives in reactions with the p-nitrophenyl esters of tert-butyloxycarbonyl-L-phenylalanine in THF. Substitution of the trimethylsilyl group for a hydrogen markedly decreases the nucleophilicity of the amino group. 2. N,O-Bis(trimethylsilyl)acetamide reacts rather rapidly with the activated ester.