Formic Acid → HCID 10321174, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (0.054 g, 0.13 mmol) in formic acid (0.16 mL, 3.0 mmol) cooled to 0° C. was treated with a 30% aqueous hydrogen peroxide solution (0.08 mL, 0.65 mmol). The resulting solution was stirred at 0° C. for 30 min and was then quenched with a 10% aqueous sodium bisulfite solution. The reaction mixture was diluted with water (5 mL) and extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was dissolved in methanol (1 mL) and was treated dropwise with a solution of potassium permanganate (0.023 g, 0.143 mmol) in water (0.5 mL). The dark brown solution was stirred at 25° C. for 30 min and then was diluted with methanol (10 mL). The reaction mixture was filtered to remove solids, and the filtrate was concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 7/3 hexanes/ethyl acetate to 1/1 hexanes/ethyl acetate) afforded 2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (33 mg, 57.3%) as a colorless gum: EI-HRMS m/e calcd for C19H20F3N3O4S (M)+ 443.1127 found 443.1137.

Provenance & Evidence