Formic Acid → HCID 10341480, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (0.060 g, 0.16 mmol) in formic acid (0.19 mL, 4.8 mmol) was cooled to 0° C. and then treated with a 30% aqueous hydrogen peroxide solution (0.10 mL, 0.8 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 (0.028 g, 0.176 mmol) in water (0.5 mL). The dark brown solution was stirred at 25° C. for 30 min, and was then 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, 1/1 hexanes/ethyl acetate to 1/4 hexanes/ethyl acetate) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (44 mg, 67.1%) as a colorless gum: C18H20ClN3O4S (M+) 409.0863, found 409.0868.

Provenance & Evidence