A general method for the synthesis of O-alkyl N,O'-arylphosphoramidates and its application to the synthesis of a transition state analogue for carbamate hydrolysis

Article abstract of DOI:10.1016/S0040-4020(98)00123-9

O-alkyl N,O'-arylphosphoramidates were synthesized by reacting phenol and aniline derivatives with alkyldichlorophosphites to form phosphoramidites followed by oxidation with mCPBA. Selective cleavage of the alkyl group under mild, neutral conditions afforded the corresponding N,O-arylphosphoramidic acids. This methodology was used to synthesize a N,O-arylphosphoramidate transition state analogue for carbamate hydrolysis.