m-Chloroperbenzoic acid → N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

Participants

Reaction Steps

To a solution of N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-vinylbenzenesulfonamide (1.5 g, 3.95 mmol) in dichloromethane (DCM) at 0° C. was added meta-chloroperoxybenzoic acid (mCPBA) (2.73 g, 15.81 mmol) and the reaction mixture stirred for 24 hours from 0° C. to 25° C. Additional mCPBA (1.364 g, 7.91 mmol) was then added and the reaction stirred for a further 6 hours. The reaction was then washed with water (2 mL), sodium hydroxide solution (2M, 2 mL) and brine (2 mL), then evaporated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% dichloromethane-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product, 926 mg, as a yellow oil. LCMS [LCMS2] Rt. 1.45, m/z (ES+) 396 (M+H).

Provenance & Evidence