Synthesis of phosphoramidate derivatives containing phthalimidomethyl group

Abstract

The derivatives of N,N-aryl(or alkyl) phthalimidomethyl phosphoramidate which is expected to exhibit biological activities are synthesized by two methods. The first method involves esterification of N,N-aryl phthalimidomethyl phosphoramidic dichlorides that obtained from reaction of phosphorus oxychcloride with N-(arylaminomethyl) phthalimides. And the second method is N-phthalimidomethylation of N-monosubstituted phosphoramidates. N-phthalimidomethylation can be accomplished in boiling benzene after deprotonation by means of sodium hydride using benzyl trimethyl ammonium chloride as a catalyst. The synthesized compounds are characterized by IR, $^1H-NMR$, $^{31}P-NMR$, and Mass spectrometry. And interesting effects on the spectral data by substitution group in the phosphoramidates are discussed.