Lithium Hydroxide → 3-[Tert-butyl-(2,4-dichlorobenzoyl)amino]-5-phenyl-thiophene-2-carboxylic acid
반응식
C[O:2][C:3]([C:5]1[S:6][C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][C:9]=1[N:10]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[C:21]([N:10]([C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[C:9]1[CH:8]=[C:7]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])([CH3:24])([CH3:22])[CH3:23]참가 물질
4
실험 절차
3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (112 mg, 0.24 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (15 mL) and then 1.5 ml of LiOH 1N was added to it. After 3 h of stirring at room temperature, solvent was removed and then partitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 32 mg (29%) of 3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid. NMR 1H (DMSO, 400 MHz): 7.62 ppm (d, 2H, Haro); 7.44-7.34 ppm (m, 4H, Haro); 7.32-7.12 ppm (m, 3H, Haro); 2.48 ppm (s, 9H).