Ammonia → 2-Carbamoylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester

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Reaction Conditions

Reaction Steps

A mixture of 2-carboxymethyl-2-(pyrrol-1-yl)-malonic acid diethyl ester (36.0 g), N-hydroxysuccinimide (16.1 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (29.2 g) in dichloromethane (200 ml) was stirred at 25° C. for 1 hour, followed by addition of 7.8% (w/w) ammonia in acetonitrile (110 ml). The resulting mixture was stirred at 25° C. for 1 hour and concentrated under reduced pressure at the same temperature. The residue was dissolved in ethyl acetate. The solution was washed with 5% hydrochloric acid and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (29.0 g, 80.8%) as colorless crystals, mp 94°-95° C.

Provenance & Evidence