Methanol → 6-[4-({[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 6-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate (0.035 g, 0.061 mmol) in tetrahydrofuran (0.6 mL) was placed in a microwave reaction tube. Methanol (0.3 mL) was added followed by 1N sodium hydroxide (0.092 mL, 0.092 mmol). The tube was sealed and heated in a microwave reactor to 100° C. for 600 seconds. The solution was neutralized and concentrated. Water was added and the mixture was filtered. The resulting solid was dried in a vacuum oven at 45° C. with P2O5 to yield the title compound (0.027 g, 77.1%) 1H NMR (DMSO-d6): 13.03 (s, 1H), 8.58 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=9 Hz, 1H), 8.03 (d, J=9 Hz, 1H), 7.96 (dd, J=2, 9 Hz, 1H), 7.90 (dd, J=2, 9 Hz, 1H), 7.81 (d, J=9, 2H), 7.42 (d, J=8 Hz, 2H), 7.25 (m, 1H), 7.14 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.35 (septet, J=7 Hz, overlapping H2O, 1H), 3.24-3.20 (m, 2H), 2.89-2.85 (m, 2H), 1.25 (d, J=7 Hz, 6H). HRMS C32H27NO4Cl2 m/z 560.1395 (M+H)+Cal; 560.1409 (M+H)+Obs.

Provenance & Evidence