Methanol → 6-(4-{[(3,5-Dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylic acid

Participants

Reaction Steps

A solution of methyl 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylate (65 mg, 0.13 mmol) in THF (1.3 mL) was placed in a microwave reaction tube. Methanol (0.7 mL) was added followed by 1.0 N sodium hydroxide (0.2 mL, 0.2 mmol) before the tube was sealed and stirred at room temperature for 30 minutes. The mixture was heated at 100° C. for 10 minutes. The solution was concentrated and the residue was suspended in water before neutralization with 1 N HCl. The resulting mixture was filtered and the sample was dried in a drying oven at 45° C. under reduced pressure with P2O5 to yield 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylic acid (0.53 g, 84%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.18-8.11 (m, 2H), 8.07 (d, J=9 Hz, 1H), 7.82 (d, J=9 Hz, 2H), 7.16 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.40-3.20 (m, overlapping H2O), 3.16-3.12 (m, 1H), 1.99 (m, 4H), 1.76-1.56 (m, 12H). HRMS C30H30N2O4 m/z 483.2278, (M+H)+Cal; 483.2277 (M+H)+Obs.

Provenance & Evidence