m-Chloroperbenzoic acid → N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide

Participants

Reaction Steps

mCPBA (60% pure, 1.70 g,) was added to a solution of N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide (1.71 g, 3.83 mmol) in chloroform (100 mL). The reaction was stirred for 4 hours and then an additional 0.57 g of mCPBA was added. The reaction was stirred for 2 more hours and then quenched by adding aqueous 1% sodium carbonate. The layers were separated and the aqueous fraction was extracted with five portions of chloroform. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to give 1.78 g of crude N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide as an orange foam.

Provenance & Evidence