Triethylamine → 3-{beta-(1-Methylimidazole-4-yl)acryloyl}amino-delta-valerolactam

Participants

Reaction Conditions

Reaction Steps

To a solution of β-(1-methylimidazole-4-yl)acrylrate hydrochloride (7 g, 37.1 mmole) in dimethylformamide (60 ml) was added triethylamine (7.51 g, 74.2 mmole) and 1-hydroxybenzotriazole hydrate (6.25 g, 40.8 mmole) and the mixture was ice-cooled, and then a solution of dicyclohexylcarbodiimide (8.42 g, 40.8 mmole) in dimethylformamide (15 ml) was added dropwise. After stirring at 80° C. for 30 minutes, followed by at room temperature for 30 minutes, 3-amino-δ-valerolactam (5.08 g, 44.5 mmole) was added to the reaction mixture which was heated with stirring for 13 hours. After cooling to room temperature, a sodium bicarbonate solution was added to the mixture which was extracted with a chloroform-methanol mixed solvent. After drying over magnesium sulfate, the solvent was removed under reduced pressure. The residue was subjected to silica gel flash chromatography and then recrystallized from ethanol/chloroform to obtain the titled compound (6.72 g, 73.0%).

Provenance & Evidence