Water → 7-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To 47 mg (0.09 mmol) of methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate in a mixture of 3 mL of EtOH, 1 mL THF and 1 mL H2O was added 35 mg (0.86 mmol) of NaOH and the mixture stirred at 50° C. for 16 hr. The mixture was concentrated to ⅓ volume then added dropwise to a a stirred solution of 10 mL of 0.5 M HCl (aq.). The resulting solids were collected by suction filtration, washed with water then dried to yield 32 mg (70%) of 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 8.97 (s, 1H), 8.24-8.21 (m, 2H), 7.99 (d, J=8 Hz, 1H), 7.76 (d, J=8 Hz, 2H), 7.63-7.61 (m, 2H), 7.55-7.52 (m, 1H), 6.93 (d, J=9 Hz, 2H), 4.88 (s, 2H), 3.50-3.44 (septet, J =7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). ESI-LCMS m/z 534 (M+H)+.

Provenance & Evidence