Ethyl Acetate → HCID 136385127, compound

Participants

Reaction Steps

To a solution of tert-butyl [6-[(Z)-amino(hydroxyimino)methyl]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.25 g, 0.54 mmol) in tetrahydrofuran (10 ml)-ethyl acetate (10 ml) was added N,N-carbonyldiimidazole (0.26 g, 1.6 mmol), and the mixture was heated under reflux for 3 hrs. The reaction mixture was partitioned between ethyl acetate and 0.1M aqueous citric acid solution. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from n-hexane-ethyl acetate to give tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)quinolin-3-yl]methylcarbamate (0.24 g, yield 90%) as a white powder.

Provenance & Evidence