Hydrochloric Acid → 2-(3-(4-(3-(2,6-Difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxamido)propanoic acid

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Reaction Steps

A mixture of Methyl 2-(3-(4-(3-(2,6-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxamido)propanoate (Example 101) (1.0 equiv.) and LiOH (3.0 equiv.) in 25 ml of 4:1 THF/water was stirred at room temperature for 15 min. The mixture was slightly acidified to pH <7 by adding 2N HCl and then the solvent was evaporated. The solid was suspended in water and filtered, given water washings and air-dried. The resulting solid was triturated with acetone and methanol and collected by filtration. This yielded the title compound as a white solid (43%) after drying in vacuo; 1H NMR (300 MHz, DMSO-d6) δ: 1.38-1.40 (d, J=7.2 Hz, 3H), 2.32 (s, 3H), 4.38-4.43 (m, 1H), 7.12-7.18 (m, 2H), 7.27-7.32 (m, 1H), 7.60 (S, 1H), 7.67-7.70 (d, J=8.4 Hz, 1H), 7.76 (s, 1H), 8.05-8.08 (d, J=8.7 Hz, 1H), 832 (s, 1H), 8.65 (s, 1H), 9.18-9.21 (d, J=7.2 Hz, 1H), 12.76 (brs, 1H); ms (ESI) m/z 445.1 [M+H]+.

Provenance & Evidence