Synthesis, Identification and in Vitro Hydrolysis of A P-Chiral Heterocyclic Phosphoramidate

Soram Ibomcha Singh and Shashi Prabha*

School of Studies in Chemistry, Jiwaji University, Gwalior (India)

Methoxy, o, p-di-chlorophenoxy, N-2-aminothiazolyl phosphoramidate has been synthesized and checked for its stability as well as reactivity near physiological conditions but in vitro. The C-N-P ester hydrolyses at pH 6.43 in 8% DMF-H2O mixture at 40(±0.5)0C and its half-life was observed to be nearly 13 hrs. The magnitude of first-order rate co-efficients observed depends upon the presence of the thiazolyl and dichloro- phenyl moieties in it. The P-N bond fission was decided by product (azo-dye test) testing during the progress of hydrolysis. Synthesis was carried out in two steps via the formation of methoxy phosphorodichloridate. Structure was confirmed by GC-MS and IR studies.

Chiral phosphoramidate; hydrolysis; physiological conditions