Novel quenchers for solution phase parallel synthesis

Abstract

The bifunctionality of amino acids can be exploited by utilizing them as quenchers in rapid solution phase parallel synthesis. The amino group was used to covalently trap the excess electrophiles, whereas the carboxylic acid moiety was used to solubilize the derivatized amino acid in water. As a prototype we used potassium sarcosinate as a quencher for excess electrophiles in the acylation or sulfonation of N-methyl-benzylamine. Various electrophilic reagents such as acid chlorides, isocyanates and sulfonyl chlorides were quenched successfully to give pure products in excellent yields.