Carbon Tetrachloride → tert-Butyl(R)-4-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

Participants

Reaction Steps

tert-Butyl((1R)-4-(2-(6-isoquinolinylcarbonyl)hydrazino)-4-oxo-1-(4-(trifluoromethyl)benzyl)butyl)carbamate (0.080 g, 0.15 mmol) and triphenylphosphine (0.070 mL, 0.30 mmol), and 0.5 mL CCl4 were heated under nitrogen in 10 mL THF at 50° C. for 20 hours. 0.2 mL DIEA was added, and the reaction mixture was heated at reflux 4 hours. The reaction mixture was filtered and the solid was washed with THF. The filtrate was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate (3×). The solvent was evaporated, and the residue was purified by chromatography on silica gel (60% EtOAc in hexane) to provide the product as a white solid (0.06 g, 78%). LCMS (API-ES) m/z: 513 (M+H+).

Provenance & Evidence