C[O:2][C:3]([C:5]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]2[C:17]([CH3:18])=[C:16]([Cl:19])[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14]2)[CH2:7][CH2:6]1)=[O:4].CCO.[OH-].[Na+]>O>[Cl:19][C:16]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14][N:13]([CH2:12][C:11]([N:8]2[CH2:7][CH2:6][C:5]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[O:24])[C:17]=1[CH3:18]In a 4 mL vial was added 100 mg of 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester (0.21 mmol, 1.0 equiv) and 400 mL EtOH. A solution of 9.2 mg of NaOH (0.23 mmol, 1.10 equiv) dissolved in 100 μL H2O was added to the reaction solution and the resultant mixture was stirred overnight at room temperature. The crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid: MS (ES) M+H expected=464.3, found=464.1.
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