Sodium Hydroxide → 5-(3-(((1-acetylpiperidin-4-yl)carbonyl)amino)phenyl)isoxazole-3-carboxylic Acid
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]3[O:23][N:22]=[C:21]([C:24]([O:26]CC)=[O:25])[CH:20]=3)[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]3[O:23][N:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=3)[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
4
Procedure
Ethyl 5-(3-{((1-acetylpiperidin-4-yl)carbonyl)amino}phenyl)isoxazole-3-carboxylate (68 g) was dissolved in THF (1.2 mL)and treated with 1N NaOH solution (1 mL) at ambient temperature for 2 hours, THF was removed under vacuo and 1N HCl was added. The mixture was extracted with ethyl acetate, dried with anhydrous Na2SO4, filtered, concentrated under vacuo to provide the title compound. MS (ESI(+)) m/e 258 (M+H)+, 375 (M+NH4)+, 380 (M+Na)+; 1H NMR (500 MHz, DMSO-d6) δ 10.14 (s, 1H), 8.20 (s, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=8.1 Hz), 7.47 (t, 1H, J=8.0 Hz), 7.20 (s, 1H), 4.40 (br d, 1H, J=12.8 Hz), 3.88 (br d, 1H, J=13.4 Hz), 3.08 (br t, 1H, J=12.9 Hz), 2.60 (m, 2H), 2.01 (s, 3H), 1.84 (m, 2H), 1.60 (m, 1H, 1.44 (m, 1H).