Benzenesulfonyl chloride → HCID 86612263, compound

Participants

Reaction Steps

mCPBA (75% purity, 4.03 g, 17.5 mmol) was added to a solution of N-[(tert-butoxycarbonyl)oxy]-2,2-dimethyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]propanamide (5.00 g, 10.0 mmol) in chloroform (975 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The mixture was cooled to 0° C. and concentrated ammonium hydroxide (20 mL) was added, followed by benzene sulfonyl chloride (2.49 mL, 19.5 mmol). The reaction mixture was stirred for 2 hours at room temperature, then was transferred to a separatory funnel. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to afford 3.35 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-[(tert-butoxycarbonyl)oxy]-2,2-dimethylpropanamide.

Provenance & Evidence