Acetone → Acitretin

HRID 2393875

Reaktionsgleichung

Reaktionsgleichung von HRID 2393875
CC[O:3][C:4](/[CH:6]=[C:7](/[CH:9]=[CH:10]/[CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]1[C:17]([CH3:26])=[CH:18][C:19]([O:24][CH3:25])=[C:20]([CH3:23])[C:21]=1[CH3:22])\[CH3:13])\[CH3:8])=[O:5].[OH-].[K+].CC(C)=O.Cl>C(O)C>[CH3:26][C:17]1[C:16](/[CH:15]=[CH:14]/[C:12](/[CH3:13])=[CH:11]/[CH:10]=[CH:9]/[C:7](/[CH3:8])=[CH:6]/[C:4]([OH:5])=[O:3])=[C:21]([CH3:22])[C:20]([CH3:23])=[C:19]([O:24][CH3:25])[CH:18]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5282375Etretinate

Produkt 1

HCID 5284513AcitretinAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Acitretin was obtained by stirring the contents of thirty 25 mg capsules of etretinate in ethyl acetate for 4 days, filtering and concentrating to dryness to give recovery of greater than 90% of the theoretical quantity of etretinate. This etretinate was then dissolved in 20 ml of ethanol, 3 ml of 4N KOH, and enough acetone to make the solution one phase. The solution was stirred at room temperature for 2 1/2 days, acidified to pH 3 with 3N HCl, and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over Na2SO4, filtered and concentrated to give a 69% yield of acitretin.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6c8a507b9443449389f53f71793864e1
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808111

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