m-Chloroperbenzoic acid → 3-[4-(2-Trifluoromethanesulfinyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-[4-(2-trifluoromethylsulfanyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Example 1; 60 mg, 0.153 mmol) in CH2Cl2 (8 mL) was cooled to 0° C. in an ice-water bath. MCPBA (130 mg, 5 equivalents) was added and the mixture was stirred at 0° C. for 1 h and then at room temperature overnight. The reaction mixture was washed with 10% aqueous Na2SO3 and saturated aqueous NaHCO3, dried (Na2SO4), filtered, evaporated and purified by chromatography (35-45% EtOAc/hexanes) to give 3-[4-(2-trifluoromethanesulfinyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (16.2 mg, 26%) as a white solid. HRMS Calcd. for C18H14F3N2O4S (M+H)+, 411.0621. Found: 411.0617.

Provenance & Evidence