Sodium Carbonate → Tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-3-yl}methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl {[6-(cyanomethoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.46 g, 1.0 mmol), hydroxyammonium chloride (0.21 g, 3.0 mmol), sodium carbonate (0.43 g, 4.0 mmol) and ethanol (10 ml) was stirred at 70° C. for 17 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 ml). 1,1′-Carbonylbis-1H-imidazole (0.32 g, 2.0 mmol) was added and the mixture was stirred at 70° C. for 24 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-3-yl}methyl)carbamate (0.18 g, yield 35%) as pale-yellow crystals.

Provenance & Evidence