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

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (6 mg, 0.01 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.020 mL, 0.020 mmol). The solution was heated in a microwave reactor at 90° C. for approximately 10 minutes and then 1 N hydrochloric acid (0.020 mL, 0.020 mmol) was added. The solution was concentrated and then dichloromethane and water were added. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (6 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.38 (d, J=8 Hz, 1H), 8.23 (d, J=8 Hz, 2H), 8.04-8.01 (m, 2H), 7.68 (d, J=9 Hz, 2H), 7.31 (s, 3H), 7.07 (d, J=9 Hz, 2H), 5.14-4.99 (m, 2H), 4.84-4.59 (m, 2H), 3.24 (septet, J=7 Hz, 1H), 1.35 (d, J=7 Hz, 6H). LRMS (APCI) m/z 595 (M+H)+.

Provenance & Evidence