Ketoprofen → Dexketoprofen

HRID 1459039

Reaktionsgleichung

Reaktionsgleichung von HRID 1459039
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)[C@@H](C1C=CC=CC=1)CN>C(C(C)=O)C(C)C>[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 3825KetoprofenHCID 10176271(S)-3-Methyl-2-phenylbutylamine

Produkt 1

HCID 667550DexketoprofenAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(±)-2-(3-Benzoylphenyl)propionic acid (20.3 g, 80 mmol) was dissolved in methyl isobutyl ketone (hereinafter abbreviated to "MIBK") (90 g) with heating. Then, (S)-(+)-3-methyl-2-phenylbutylamine (6.68 g, 41 mmol) was added dropwise with stirring at 40° C. After completing the addition, the reaction solution was stirred at 40° C. for one hour and then cooled slowly to 10° C. over 6 hours. After stirring at 10° C. for 3 hours, the precipitated crystal was filtered and the filter cake was washed with cold MIBK (50 ml) and then dried. In this manner, a diastereomer salt (11.5 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine was obtained.

Aufarbeitung

  1. temperaturewith heating
  2. additionthe addition
  3. stirringthe reaction solution was stirred at 40° C. for one hour
  4. temperaturecooled slowly to 10° C. over 6 hours
  5. stirringAfter stirring at 10° C. for 3 hours
  6. filtrationthe precipitated crystal was filtered
  7. washthe filter cake was washed with cold MIBK (50 ml)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c26188f9388c46a987091d27a6c887f5
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852209

Verknüpfte Notizen

Wird geladen…