Hydrochloric Acid → HCID 22175663, compound

Participants

Reaction Conditions

Reaction Steps

To a solution (30 mL) of tert-butyl(6-cyano-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.86 g, 2.0 mmol) in toluene were added sodium azide (0.16 g, 2.5 mmol) and triethylamine hydrochloride (0.28 g, 2.5 mmol) and the mixture was stirred at 90° C. for 24 h. The reaction mixture was poured into water (100 mL), acidified with 1N hydrochloric acid and extracted twice with ethyl acetate (50 mL). The extracts were combined and washed with saturated brine (15 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran-diisopropyl ether (1:5) to give tert-butyl [2-isobutyl-1-oxo-4-phenyl-6-(2H-tetrazol-5-yl)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.36 g, 37%) as colorless crystals.

Provenance & Evidence