[OH-].[Na+].[Cl:3][C:4]1[CH:23]=[C:22]([NH:24][C:25](=[O:39])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:29]=2[Cl:38])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]1.Cl>CCO>[Cl:3][C:4]1[CH:23]=[C:22]([NH:24][C:25](=[O:39])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][C:29]=2[Cl:38])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]12 mL aqueous NaOH (1 M) was added at RT to a solution of 150 mg (0.270 mmol) ethyl 1-(2-{2-chloro-4-[2-(2-chloro-4-trifluoromethyl-phenoxy)-acetylamino]-phenoxy}-ethyl)-piperidine-4-carboxylate (Example 146) in 4 mL EtOH and the mixture was stirred for 16 h. The reaction mixture was neutralised with 2 mL aqueous HCl (1 M), evaporated down i. vac. and the crude product was purified by column chromatography (silica gel, dichloromethane/MeOH 4:1).
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