Tetrahydrofuran → HCID 22175381, compound

Participants

Reaction Steps

A mixture of ethyl trifluoroacetate (0.038 mL, 0.31 mmol) and hydrazine monohydrate (0.026 mL, 0.50 mmol) in tetrahydrofuran (3 mL) was refluxed in a sealed tube for 1 h, the reaction was allowed to cool to room temperature. To the mixture were added tert-butyl{6-[amino(imino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate diacetate (0.14 g, 0.25 mmol) and sodium hydroxide (0.027 g, 0.55 mmol), and the resulting mixture was refluxed for 3 h. The reaction mixture was partitioned between water (10 mL) and ethyl acetate (30 mL). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel-column chromatography (n-hexane:ethyl acetate=3:1 (v/v)) to give tert-butyl{2-isobutyl-1-oxo-4-phenyl-6-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.074 g, 55%) as a colorless powder.

Provenance & Evidence