(Diethylamino)sulfur trifluoride → 4-[(Dimethoxy-phosphoryl)fluoro-methyl]-benzoic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

4-[(Dimethoxy-phosphoryl)-hydroxy-methyl]-benzoic acid benzyl ester (0.20 g, 0.22 mmol) was added over 30 mins to a stirring solution of DAST (1M in CH2Cl2) cooled to −78° C. under a dry nitrogen environment. The mixture was warmed to RT and stirred for 18 hours. The reaction mixture was then quenched with ethanol containing pyridine (pyr: twice volume of DAST). After another 30 mins the mixture was poured into ice cold water and extracted into DCM (3×). The combined organic extracts were washed with dilute aq HCl, water, brine, dried (MgSO4) then concentrated in vacuo. The residue was purified by HPLC (20-85% MeCN in Water w/0.025% TFA) to afford the title compound: MS: cal'd 353 (MH+), exp 353 (MH+)

Provenance & Evidence