2,6-Lutidine → HCID 86738872, compound

Participants

Reaction Steps

To a solution of methyl 4-[(2R,3R)-3-formamido-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (133 mg) and 2,6lutidine (0.96 ml) in dichloromethane (3 ml) was added phosphorus oxychloride (0.15 ml) at 0°. After stirring at the same temperature for four hours, the reaction mixture was diluted with ethyl acetate (20 ml), and washed with a dilute aqueous sodium chloride, dilute phosphoric acid, a dilute aqueous sodium chloride, ice-water, and a saturated aqueous solution of sodium chloride in turn. Drying over magnesium sulfate and removal of the solvent gave a brown oil, which was chromatographed on silica gel (2 g) eluting with 3% methanol in dichloromethane to give methyl 4-[(2R,3R)-3-isocyano-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (70 mg) as a crystalline solid

Provenance & Evidence