Hydrochloric Acid → 3-Bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acid
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:31][CH2:30][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([O:7]C)=[O:6].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:27][CH2:28][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][CH2:31]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([OH:7])=[O:6]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
To the title compound of Example 224 Step D (0.07 mmol, 40 mg) in 2 mL of dioxane was added a solution of LiOH (1 mmol, 24 mg) in 1 mL of H2O. The reaction was allowed to stir at 40° C. for 1.5 h. The crude reaction mixture was poured into pH 7 buffer/EtOAc, which was acidified with 2 N HCl until two clear layers formed after agitation. The organic phase was collected and the aqueous phase was extracted twice with EtOAc. The combined organic phase was dried over Na2SO4, then concentrated under reduced pressure to afford the product as a slightly yellow-green foam. HPLC A: 2.32 min.
Aufarbeitung
- customThe crude reaction mixture
- customformed after agitation
- customThe organic phase was collected
- extractionthe aqueous phase was extracted twice with EtOAc
- dry with materialThe combined organic phase was dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customto afford the product as a slightly yellow-green foam
- custom2.32 min.
Quellen und Nachweise
- ORD-Eintrag
- ord-4776b4418b33418490a2decccacea137
- Quelldatensatz
- uspto-grants-2009_07
- Patentnummer
- US07563815B2
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