Application of 4-Alkoxy-1,1,1-trifluoro[chloro]alk-3-en-2-ones as Selective Protecting Groups of Amino Acids

Abstract

A convenient selective protection of the α-amino carboxyl group of amino acids bearing reactive side chain groups such as arginine, asparagine, glutamine, cysteine, histidine, serine and lysine, using 4-alkoxy-1,1,1-trifluoro[chloro]alk-3-en-2-ones is reported. The reactions were performed without esterification of the carboxyl group and N-deprotection was carried out using a six molar solution of hydrochloric acid.

Key words

ketones - fluorine - halogens - amino acids - protecting groups

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Handbook of Fine Chemicals and Laboratory Equipment, Aldrich, 2001-2002.