Phosphorus-containing aminocarboxylic acids. 1. Method of preparation of phosphonate-type compounds

A method is described for the synthesis of phosphorus-containing amino carboxylic acids, by the Michaelis-Bekker or Arbuzov phosphorylation of -haoalkylacetamidomalonic esters. The latter were obtained by alkylating the sodium salt of acetamidomalonic ester with an excess of the ,-dihaloalkane. Acid hydrolysis of the phosphorus-containing alkylacetamidomalonic esters gave the required compounds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2590–2595, November, 1989.     

PHOSPHORUS-CONTAINING AMINOCARBOXYLIC ACIDS. COMMUNICATION IV.1 A CONVENIENT METHOD OF PHOSPHONIC ACIDS SYNTHESIS

Abstract

The communication is concerned with the synthesis of phosphonic aminocarboxylic acids by phosphorylation of diethyl ω-halogen alkyl acetamidomalonates with tris(trimethylsilyl) phosphite, followed by alcoholysis and acid hydrolysis of the resulting intermediate esters.