Sodium Hydroxide → 4-Methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid
Reaktionsgleichung
C([O:3][C:4](=[O:38])[CH:5]([C:10]1[CH:11]=[C:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:33]=2)[CH:13]=[C:14]([CH:16]2[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[CH2:20][CH2:21]2)[CH:15]=1)[C:4]([OH:38])=[O:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of a mixture of 4-methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester and methyl ester (26 mg, 0.05 mmol) in MeOH (1 mL) was added 3N NaOH (0.100 mL) and heated to 50° C. for 2 h. The reaction was concentrated in vacuo to remove MeOH. The thick liquid was acidified to pH=2 by 2N HCl. The resulting acidic solution was extracted with EtOAc. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by Gilson reverse phase column chromatography to obtain 4-methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid.
Aufarbeitung
- concentrationThe reaction was concentrated in vacuo
- customto remove MeOH
- extractionThe resulting acidic solution was extracted with EtOAc
- dry with materialThe organic fraction was dried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude mixture was purified by Gilson reverse phase column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-b9e5f37954644aaf852f3913ae0f9eff
- Quelldatensatz
- uspto-grants-2012_08
- Patentnummer
- US08252935B2
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