Ketoprofen → Dexketoprofen

HRID 1459041

Reaktionsgleichung

Reaktionsgleichung von HRID 1459041
[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>CC(CC(C)=O)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 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

(±)-2-(3-Benzoylphenyl)propionic acid (12.7 g, 50 mmol) was added to MIBK (70 ml) and dissolved with heating to 35° C. Then, (S)-(+)-3-methyl-2-phenylbutylamine (5.24 g, 32 mmol) was added dropwise with stirring. After completing the addition, the reaction solution was stirred at 35° C. to 40° C. for one hour, followed by at room temperature for 5 hours and then at 10° C. for 2 hours. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (30 ml) and dried to give a diastereomer salt (8.76 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine. The yield of the product based on (S)-(+)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 84%.

Aufarbeitung

  1. dissolutiondissolved
  2. additionthe addition
  3. stirringthe reaction solution was stirred at 35° C. to 40° C. for one hour
  4. waitat 10° C. for 2 hours
  5. customThen, the crystal precipitated
  6. filtrationwas filtered
  7. washthe filter cake was washed with cold MIBK (30 ml)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3ec9a513ea0b4fe59439b021dcfc04e3
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852209

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