Ketoprofen → Dexketoprofen

HRID 1459042

Reaktionsgleichung

Reaktionsgleichung von HRID 1459042
[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: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 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

(±)-2-(3-Benzoylphenyl)propionic acid (12.7 g, 50 mmol) was added to methyl ethyl ketone (hereinafter abbreviated to "MEK") (70 ml) and dissolved with heating. Then, (S)-(+)-3-methyl-2-phenylbutylamine (4.9 g, 30 mmol) was added dropwise with stirring. After completing the addition, the reaction solution was stirred at 35°C. to 40°C. for one hour and then at room temperature for 4 hours, and finally maintained at 10°C. for 3 hours. The crystal precipitated was filtered, and the filter cake was washed with cold MEK (35 ml) and dried to give a diastereomer salt (7.72 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 74%.

Aufarbeitung

  1. dissolutiondissolved
  2. temperaturewith heating
  3. additionthe addition
  4. stirringthe reaction solution was stirred at 35°C. to 40°C. for one hour
  5. customThe crystal precipitated
  6. filtrationwas filtered
  7. washthe filter cake was washed with cold MEK (35 ml)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9ca4ba25cea346afb2de01712e165811
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852209

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