Reaktionsgleichung
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].C1(C)C=CC=CC=1.[CH2:23]([NH:31][CH2:32][C@@H:33]([C@H:35]([C@@H:37]([C@@H:39]([CH2:41][OH:42])[OH:40])[OH:38])[OH:36])[OH:34])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O>[CH2:23]([NH:31][CH2:32][C@@H:33]([C@H:35]([C@@H:37]([C@@H:39]([CH2:41][OH:42])[OH:40])[OH:38])[OH:36])[OH:34])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[OH:3][C:2]([C@H:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:14][CH:15]=1)[CH3:5])=[O:1]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 78 °C
Versuchsvorschrift
Racemic ibuprofen (80 g, 390 mmol), toluene (200 mL), and water (0.5 mL) were stirred at 40° C., and N-octyl-D-glucamine (53.8 g, 183 mmol, N-octyl-D-glucamine/(S)-ibuprofen molar ratio=0.938) was added to the solution. The resulting thick slurry was heated to 78° C., forming a clear solution, and the solution then cooled to 15° C. over 3-4 hours. The resulting precipitate was recovered by filtration, washed with toluene (100 mL), and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (72.2 g, 145 mmol, 74.6% yield, MR=136°-137° C.). The toluene liquors were saved for racemization and recycle of the contained (R)-ibuprofen.
Aufarbeitung
- customforming a clear solution
- temperaturethe solution then cooled to 15° C. over 3-4 hours
- filtrationThe resulting precipitate was recovered by filtration
- washwashed with toluene (100 mL)
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-2a02f8d28637400f94587b44e51137d6
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05621140
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