Hydrochloric Acid → HCID 54725316, compound

Participants

Reaction Steps

To a suspension of 4-benzyloxyphthalic anhydride (2.54 g, 10 mmol) in ethanol (30 mL) was added 20% sodium ethoxide ethanol solution (3.74 g, 11 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (150 mL) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (200 mL) and tert-butyl 2-(isobutylamino)acetate (2.25 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12 mmol) and 1-hydroxybenzotriazole (1.84 g, 12 mmol) were added and the mixture was stirred at room temperature for 3 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 dissolved in ethanol (30 mL) and a solution (6.80 g, 20 mmol) of 20% sodium ethoxide in ethanol was added thereto. The mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (20 mL) 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 and the component eluted earlier was concentrated to give tert-butyl 7-benzyloxy-4-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (0.40 g, 9.5%) as an oil.

Provenance & Evidence