2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole → 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanol

Participants

Reaction Steps

To a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole in CH3CN (1 mL) was added a 5% solution of aqueous HF in CH3CN (3 mL). The reaction was complete in 1 h and the crude product was extracted with EtOAc (3×75 mL). The combined extracts were washed with H2O and brine, and dried over anhyd Na2SO4, concentrated and purified by flash chromatography (20% MeOH/DCM) to yield the title compound (493 mg, 95%) as a white solid. MS (EI) m/z 563.30 (MH+).

Provenance & Evidence