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

HRID 54037

Reaktionsgleichung

Reaktionsgleichung von HRID 54037
[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].[CH3:16][NH:17][CH2:18][C@@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])[OH:20].O>C1(C)C=CC=CC=1>[CH3:16][NH:17][CH2:18][C@@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])[OH:20].[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

HCID 962WaterHCID 3672Ibuprofen, (+-)-HCID 8567N-Methyl-D-glucamine

Produkt 1

HCID 15008340(S)-ibuprofen N-methyl-D-glucamine saltAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Racemic ibuprofen (18.03 g, 87.4 mmol), N-methyl-D-glucamine (8.2 g, 42 mmol), water (0.5 mL), and toluene (150 mL) were heated to 50° C., forming a clear solution. The solution was cooled to 20° C., then in an ice bath, and allowed to stand for 48 hours. The resulting crystalline precipitate was recovered by filtration at 20° C., washed with toluene (30 mL), and dried to give (S)-ibuprofen N-methyl-D-glucamine salt (11.9 g, 68% yield, 92% ee).

Aufarbeitung

  1. customforming a clear solution
  2. customin an ice bath, and allowed
  3. filtrationThe resulting crystalline precipitate was recovered by filtration at 20° C.
  4. washwashed with toluene (30 mL)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1abc6ef7eb914200a27aa0025599194d
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621140

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