Lithium Hydroxide → HCID 10256736, compound

Participants

Reaction Steps

A solution of methyl 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)amino]methyl}benzoate (0.42 g, 0.76 mmol) in tetrahydrofuran (4 mL) was stirred vigorously with aqueous lithium hydroxide (2.3 ml, 0.4 M) at ambient temperature for 24 hours. The reaction was concentrated and the aqueous residue was partitioned with ethyl acetate and aqueous sodium hydrogensulfate. The organic layer was washed with brine (50 mL) and was dried over anhydrous magnesium sulfate, filtered, and condensed to a residue which was chromatographed on silica gel eluting with 10% methanol/dichloromethane. Yield=0.12 g. (30%) of 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)amino]methyl}benzoic acid. 1H NMR (CDCl3, 400 MHz) δ 8.02 (s, 1H), 7.91 (d, 1H), 7.55 (d, 1H), 7.38 (m 3H), 7.31 (m, 1H), 6.95 (d, 1H), 6.33 (m, 1H), 6.57 (dd, 1H), 4.67 (s, 2H), 3.97 (s, 2H), 3.91 (s, 3H), 3.31 (m, 1H), 2.49 (s, 3H), 2.33 (s, 3H), 1.40 (d, 6H); MS (ESP+) m/e 539 (MH+).

Provenance & Evidence