Synthesis of N-phosphoryl amino acids using bis(9-fluorenylmethyl)phosphite

Abstract

Bis(9-fluorenylmethyl)phosphite (BFMP) was found to be an effective reagent for the N-phosphorylation of various amino acid methyl esters. BFMP was prepared from N, N-diisopropyl phosphoramidous dichloride in a one-pot two-step reaction and was obtained as a crystalline solid. N-Phosphorylation of the methyl esters of seven representative amino acids with BFMP was high-yielding and generally resulted in crystalline products. Complete deprotection of both the 9-fluorenylmethylphosphosphate esters and the amino acid methyl esters was accomplished concomitantly with LiOH to give N-phosphoryl amino acids.