Citric Acid → HCID 22176007, compound

Participants

Reaction Steps

A mixture of (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)acetic acid (0.15 g, 0.32 mmol), 1-hydroxybenzotriazole ammonium salt (0.074 g, 0.48 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.093 g, 0.48 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 17 h. The reaction mixture was poured into 0.1N aqueous citric acid solution (50 mL) and extracted with ethyl acetate (25 mL×2). The organic layers were combined, washed with 0.1N aqueous citric acid solution (50 mL), saturated aqueous sodium hydrogencarbonate (50 mL), and brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give tert-butyl[6-(2-amino-2-oxoethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.12 g, 81%) as colorless crystals.

Provenance & Evidence