Water → Methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate

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Reaction Steps

A mixture of benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate (400 mg, 1 mmol) in phosphoryl trichloride (5 mL) was heated to reflux for 40 mins. The mixture was cooled to room temperature and poured into water (100 mL) carefully with vigorous stirring, then extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=30:1 to 8:1) to give methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate (170 mg, yield 45%). LC-MS (ESI) m/z: 381 (M+1).

Provenance & Evidence