Pyridine → HCID 22176256, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl{6-[amino(hydroxyimino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.23 g, 0.50 mmol) and pyridine (0.043 mL, 0.53 mmol) in toluene (20 mL), was added ethyl chlorooxoacetate (0.059 mL, 0.53 mmol), and the mixture was stirred at room temperature for 1 h and at 80° C. for 1 h. The reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1–1:3 (v/v)) and recrystallized from diisopropyl ether-ethyl acetate (20:1, v/v, 5 mL) to give ethyl 3-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)-1,2,4-oxadiazole-5-carboxylate (0.13 g, 48%) as colorless crystals.

Provenance & Evidence