Water → (S)-ibuprofen N-octyl-D-glucamine salt

HRID 54035

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].[CH2:16]([NH:24][CH2:25][C@@H:26]([C@H:28]([C@@H:30]([C@@H:32]([CH2:34][OH:35])[OH:33])[OH:31])[OH:29])[OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH2:16]([NH:24][CH2:25][C@@H:26]([C@H:28]([C@@H:30]([C@@H:32]([CH2:34][OH:35])[OH:33])[OH:31])[OH:29])[OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[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

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

Racemic ibuprofen (18.03 g, 87.4 mmol), N-octyl-D-glucamine (12.12 g, 41.3 mmol), triethylamine (4.4 g, 43.5 mmol), water (0.5 mL), and toluene (150 mL) were heated to 80° C., forming a clear solution. The solution was cooled to 25° C. over 2 1/2 hours, then cooled in an ice bath to 15° C. The resulting crystalline precipitate was recovered by filtration, washed with toluene, and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (17.2 g, 78.8% yield, 94.8% ee).

Aufarbeitung

customforming a clear solution
temperaturecooled in an ice bath to 15° C
filtrationThe resulting crystalline precipitate was recovered by filtration
washwashed with toluene
customdried

Quellen und Nachweise

ORD-Eintrag: ord-35ee6ae184d34e9e99eed5912c2385b9
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05621140

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