Peracetic Acid → HCID 67051109, compound

Participants

Reaction Steps

Peracetic acid (2.0 mL of 32% by weight in dilute acetic acid, 9.5 mmol) was added to a solution of (8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (2.5 g, 6.2 mmol) in ethyl acetate (400 mL), and the reaction was stirred for two days at ambient temperature. The volatiles were removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed with aqueous sodium bicarbonate and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from a mixture of ethyl acetate, hexanes, and 2-propanol and then purified by column chromatography on a HORIZON HPFC system (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 90:10) to provide 1.9 g of (8-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a solid, mp 228-230° C.

Provenance & Evidence