Dimethyl Sulfoxide → 4-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.2 mL, 2.2 mmol) in anhydrous dichloromethane (2 mL) at −78° C. was added DMSO (0.32 mL, 4.5 mmol) under Argon. The solution was maintained for 10 min where upon a solution of 4-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide (430 mg, 1.5 mmol) in anhydrous dichloromethane (13 mL) was added dropwide. The reaction was stirred at −78° C. for 30 min, whereupon TEA (1 mL, 7.5 mmol) was added. The reaction was warmed to 22° C. for 2 h. Then, 50 mL dichloromethane was added to the mixture, washed with sat NaHCO3 (3×15 mL) and sat. brine (3×15 mL), dried (MgSO4), and concentrated to afford a yellow solid of 4-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide. MS (ESI) 287 (M+H)+.

Provenance & Evidence