Efficient and Practical Procedure for the Esterification of the Free alpha-Carboxylic Acid of Amino Acid Residues with beta-(Trimethylsilyl)ethoxymethyl Chloride and Triisopropylsilyl Chloride

An efficient and practical procedure for the free -carboxylic acid esterification of amino acid residues with -(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride is described. The reaction takes place under mild conditions and the expected protected amino acids are obtained in good to excellent yields. Our method provides a useful alternative for the C-terminal carboxylic acid protection of amino acids and peptides. Moreover, the removal of such protection was also achieved under mild conditions, without affecting either the other protecting groups at the -amino moiety and side chains or the optical integrity at the -position of the amino acid residues. Examples of their use in peptide synthesis are also illustrated. (AU)