Water → HCID 178498873, compound

Participants

Reaction Steps

To a mixture of tert-butyl{6-[amino(hydroxyimino)-methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.47 g, 1.0 mmol) and triethylamine (0.17 mL, 1.2 mmol) in ethyl acetate (10 mL) was added methylpropionate (0.10 g, 1.2 mmol), and the mixture was stirred at room temperature for 17 h. The reaction mixture was poured into water (5 mL), and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added p-xylene (10 mL), the mixture was refluxed for 40 h. The reaction mixture was diluted with ethyl acetate (100 mL), and the solution was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v)) to give methyl 2-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)-1H-imidazole-4-carboxylate (0.22 g, 42%) as an orange powder.

Provenance & Evidence