Sodium Hydroxide → HCID 59759162, compound

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][C:14]1[N:15]=[C:16]([S:19][C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[S:17][CH:18]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][C:14]3[N:15]=[C:16]([S:19][C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[S:17][CH:18]=3)=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:31][CH:32]=1

Participants

Procedure

4-(2-{2-[(2-tert-Butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethoxy)-4′-fluoro-biphenyl-3-carboxylic acid methyl ester (1.6 g) synthesized in Example 92-2 was dissolved in methanol (15 mL) and tetrahydrofuran (20 mL), aqueous sodium hydroxide solution (1 mol/L, 15 ml) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, aqueous 10% citric acid solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.3 g) as an oil.