m-Chloroperbenzoic acid → HCID 15952273, compound

Participants

Reaction Steps

To a solution of 10-{[2′-(1-hydroxyethyl)-1,1′-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 52 (0.500 g, 0.92 mmol) in dichloromethane (20 mL) was added saturated aqueous sodium hydrogencarbonate solution (20 mL) followed by 70% 3-chloroperoxybenzoic acid (909 mg, 3.69 mmol) and the biphasic mixture was stirred vigorously for 1 hour. The reaction was quenched by the addition of 5% aqueous sodium metabisulfite solution (20 mL), the mixture stirred vigorously for 5 minutes, then partitioned between ethyl acetate (100 mL) and 2 M sodium hydroxide (100 mL). The organic layer was separated, washed with 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a white solid. Purification by flash chromatography using a solvent gradient of 3 to 10% methanol in dichloromethane gave the title compound (31.1 mg, 6%) as a white solid, m.p. 213-215° C.

Provenance & Evidence