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The syntheses of 4-(Boc-aminoacyloxymethyl)-3-nitrobenzoic acids are described. These compounds are suitable reagents for coupling to polyethylene glycol or its derivatives by the dicyclohexylcarbodiimide method to obtain 4-(Boc-aminoacyloxymethyl)-3-nitrobenzoyl-polyethylene glycol support. This is demonstrated by the reaction of the 4-carboxy-2-nitrobenzyl ester of Boc-alanine with glycylpolyethylene glycol in excellent yield. This synthetic route produces a much better coupling yield and an easier purification procedure in comparison with the original method in which Boc-amino acid cesium salts are allowed to react with 4-(bromomethyl)-3-nitrobenzoyl-polyethylene glycol.

Syntheses of 4-[N-(tert-Butoxycarbonyl) aminoacyloxymethyl]-3-nitrobenzoic Acids for Use in the Liquid-Phase Peptide Synthesis