Sodium Hydroxide → 5-n-Butyl-2-(5-carboxy-2-chlorophenyl)-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
Reaktionsgleichung
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:47])(=[O:46])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:25][CH:24]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:46])(=[O:47])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:27][CH:28]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
A solution of 71 mg (0.102 mmole) of 5-n-butyl-2-[5-(carbomethoxy)-2-chlorophenyl]-4-[[2'-[N-(2-chlorobenzoyl)-sulfamoyl]-biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 65, Step D) in 0.7 mL (0.7 mmole) of 1N NaOH (methanolic) was stirred at 60° C. overnight and then concentrated to dryness. The residue was dissolved in 1 mL of methanol, acidified to approximately pH 1.5 by addition of 1N HCl (methanolic), and again concentrated. The residue was dissolved in CHCl3, dried over Na2SO4, and filtered through Celite. Evaporation of the solvent yielded 58 mg (84%) of the title compound as a white solid; nearly homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 679 (M+1)+.