Acetamidomalonic acid diethyl ester → HCID 21834431, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (52 mg of 60% oil dispersion, 1.30 mmol) was added to a solution of 310 mg (1.43 mmol) of diethyl acetamidomalonate in 2.0 mL of N,N-dimethylformamide. After 30 min, 72 mg (0.20 mmol) of tetrabutylammonium iodide was added followed by 200 mg (0.65 mmol) of 6 -(2-methanesulfonyloxyethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine in 1.0 mL of N,N-dimethylformamide. The reaction was stirred at room temperature for 30 min, at 60° C. for 20 h, and at room temperature for 3 d. The reaction was diluted with 30. mL of ethyl acetate and washed with 15 mL each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The aqueous layers were extracted in succession with 30 mL of ethyl acetate. The combined organic layers were dried (sodium sulfate), decanted, and evaporated. The crude product was purified by flash column chromatography on 15 g of silica gel, eluting with 300 mL of 10% ethyl acetate in dichloromethane to give 243 mg (87% yield) of diethyl 2-acetamido-2-(2-(6-amino-4-methylpyrid-2-yl)ethyl)malonate as a tan solid.

Provenance & Evidence