Preparation of dimethyl ( R)- and ( S)-2-(2-aminophenyl)-2-hydroxyethylphosphonate from anthranilic acid

Abstract

An efficient synthesis of both enantiomers of dimethyl δ-amino-β-hydroxyethylphosphonate 6 has been achieved starting from anthranilic acid, through the resolution of dimethyl (±)-2-(2- N, N-dibenzylaminophenyl)-2-hydroxyethylphosphonate 9 with ( S)- O-methylmandelic acid. The absolute configuration of the enantiomers 9 was assigned by the Dale and Mosher approach using the extended Newman projections and molecular mechanics.