Water → HCID 22175628, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl[6-hydroxy-2-isobutyl-4-phenyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.42 g, 1 mmol) in N,N-dimethylformamide (10 ml) was added sodium hydride (48 mg, 1.2 mmol) (60% in oil). The resulting mixture was stirred at 0° C. for 10 min. To the mixture was added methyl 2-bromoisobutyrate (0.22 g, 1.2 mmol), and the mixture was stirred at room temperature for 12 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give methyl 2-[(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)oxy]-2-methylpropanoate (0.31 g, 59.6%) as crystals.

Provenance & Evidence