Synthesis of 2-alkoxy-2-acylaminopropionic acids by alkoxymercuration–demercuration of 2-acylaminoacrylic acids

Abstract

Alkoxymercuration of 2-acylaminoacrylic acids (1) with alcohols and mercury(II) acetate, followed by demercuration with sodium borohydride in aqueous sodium hydroxide, leads to 2-alkoxy-2-acylaminopropionic acids, together with the starting acids. The products have been isolated as the methyl esters. The orientation of the addition to the ethylenic double bond is controlled by mesomeric donation by the nitrogen atom.