Author/Authors :
Vepsalainen، Jouko نويسنده , , Huttunen، Kristiina M. نويسنده , , Kumpulainen، Hanna نويسنده , , Leppanen، Jukka نويسنده , , Rautio، Jarkko نويسنده , , Jarvinen، Tomi نويسنده ,
Abstract :
A novel method for the synthesis of water-soluble ketoxime phosphate prodrugs avoiding the unwanted Beckmann rearrangement is developed. In the first step, a novel in situ prepared phosphorochloridic acid bis-(2-trimethylsilyl-ethyl) (TMSE) ester 1 reacts with the hydroxyimine 2. In the second step, the formed TMSEphosphate triester 3 undergoes a tetrabutylammonium fluoride mediated microwave-assisted conversion into the corresponding ketoxime phosphate salt 4 without further Beckmann rearrangement.
Keywords :
imines , ketones , prodrugs , Beckmann rearrangement , protecting grou
