[Study on the phosphorylaions reaction between ethyl salicylate and DEPH].
Atherton-Todd reaction has been extensively applied to the synthesis of phosphates and phosphoroamidates. Under Atherton-Todd reaction conditions, dialkyl phosphites were probably transformed into diakyl phosphorochloridates. We have tried to use Atherton-Todd reaction to synthesize phosphate of salicylic-acid. But when the -COOH of salicylic acid was under unprotected, the yield was quite low. It was found that the -COOH possibly participated in the reaction. The competitive reaction between the -COOH and -OH of salicylic acid probably existed. In order to understand the detail mechanism, ethyl-salicylate was selected to be phosphorylated In the end, ethyl-salicylate successfully phosphorylated by modification of the classical Atherton-Todd procedure through dropping the DEPH and tetrachloromethane into the mixed solution of ethyl-salicylate, triethylamine and dioxane with good yields. The structures were elucidated by NMR and ESI/MS/MS data.
Chen
Xiao-lan
XL
Chemistry Department, Zhengzhou University, Zhengzhou, China.
Liao
Xin-cheng
XC
Lu
Jian-sha
JS
Guo
Lei
L
Qu
Ling-bo
LB
Zhao
Yu-fe
YF
D008958:Models, Molecular; D010766:Phosphorylation; D011073:Polyamines / Q000737:chemistry*; D012459:Salicylates / Q000737:chemistry*; D013055:Spectrophotometry, Infrared / Q000379:methods*; D014862:Wasp Venoms / Q000737:chemistry*
D011073:Polyamines; D012459:Salicylates; D014862:Wasp Venoms; C069952:dephenol-PTX-4.3.3; C041835:ethyl salicylate