Ethanol → Dexibuprofen lysine anhydrous

HRID 1589944

Reaktionsgleichung

Reaktionsgleichung von HRID 1589944
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:11][C@H:12]([C:23]([OH:25])=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=1.C(O)C>C(O)C.O>[CH3:11][C@H:12]([C:23]([OH:25])=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:21])[CH3:22])=[CH:15][CH:14]=1.[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 5962L-Lysine2×HCID 39912Dexibuprofen

Produkt 1

HCID 9819903Dexibuprofen lysine anhydrousAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A 500 ml 3 neck flask equipped with mechanical stirrer and thermometer was charged with H2O (42 ml) and L-lysine (37.5 g, 0.25 mole). The mixture was agitated until a solution was obtained. A solution of S(+)-ibuprofen in absolute ethanol (52.6 g, 0.25 mole in 250 ml ethanol) was made up and added to the aqueous lysine over 5 minutes at a temperature ≤35° C. The resulting solution was filtered through a sintered glass funnel (medium frit) to remove any insoluble material. The filtrate was transferred to a 3000 ml 3-neck flask equipped with a mechanical stirrer, addition funnel and thermometer. To this clear solution was added 575 ml of ethanol over 5 minutes at 20°-25° C. The turbid solution was seeded with the L-lysine salt of S(+)-ibuprofen (50 mg) and an additional 400 ml of ethanol was added over 10 minutes. The resulting suspension was aged at 20°-25° C. for 1 hour with agitation, cooled to 0°-5° C. and held for 1 hour. The product was filtered, washed with 5°±5° C. ethanol (2×1 mmol) and dried in vacuo (50° C.) to yield 74 g (84%) of the titled compound. [α]405 =+14.9° C. (C=1, methanol).

Aufarbeitung

  1. customwas obtained
  2. filtrationThe resulting solution was filtered through a sintered glass funnel (medium frit)
  3. customto remove any insoluble material
  4. customThe filtrate was transferred to a 3000 ml 3-neck flask
  5. customequipped with a mechanical stirrer, addition funnel
  6. additionTo this clear solution was added 575 ml of ethanol over 5 minutes at 20°-25° C
  7. additionan additional 400 ml of ethanol was added over 10 minutes
  8. temperaturecooled to 0°-5° C.
  9. waitheld for 1 hour
  10. filtrationThe product was filtered
  11. customdried in vacuo (50° C.)

Quellen und Nachweise

ORD-Eintrag
ord-dac1272f92ad4bb491ceebf34e7736f2
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200558

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