An efficient strategy for the synthesis of 1-chloroethyl phosphates and phosphoramidates.
[reaction: see text] A versatile, efficient, and simple method for the preparation of various 1-chloroethyl phosphates and phosphoramidates is described. The protected chlorophosphates or phosphoramidates are synthesized to the vinyl derivative under mild conditions, followed by conversion to the chloroethylidene phosphate or phosphoramidate by dry HCl gas, resulting in good to excellent yields. 1-Chloroethyl phosphates and phosphoramidates are excellent building blocks for the synthesis of novel ethylidene-linked phosphate prodrugs.
Kumpulainen
Hanna
H
Department of Pharmaceutical Chemistry, University of Kuopio, Finland. Hanna.Kumpulainen@uku.fi
Järvinen
Tomi
T
Saari
Raimo
R
Lehtonen
Marko
M
Vepsäläinen
Jouko
J
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D015394:Molecular Structure; D010710:Phosphates / Q000138:chemical synthesis / Q000737:chemistry*; D010756:Phosphoric Acids / Q000138:chemical synthesis / Q000737:chemistry*
D000577:Amides; D010710:Phosphates; D010756:Phosphoric Acids; D002713:Chlorine; C011067:phosphoramidic acid