Fluticasone → Fluticasone Propionate

HRID 1272567

Reaktionsgleichung

Reaktionsgleichung von HRID 1272567
[CH3:1][C@H:2]1[C@:19]([OH:25])([C:20]([S:22][CH2:23][F:24])=[O:21])[C@:18]2([CH3:26])[C@H:4]([C@H:5]3[C@:15]([F:28])([C@@H:16]([OH:27])[CH2:17]2)[C@:14]2([CH3:29])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[C@@H:7]([F:30])[CH2:6]3)[CH2:3]1>CO.ClCCl>[CH3:8][CH2:9][C:10]([O:25][C@@:19]1([C:20]([S:22][CH2:23][F:24])=[O:21])[C@@:18]2([CH3:26])[CH2:17][C@H:16]([OH:27])[C@:15]3([F:28])[C@:14]4([CH3:29])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]4)=[O:11])[C@@H:7]([F:30])[CH2:6][C@H:5]3[C@@H:4]2[CH2:3][C@H:2]1[CH3:1])=[O:11]

Komponenten

4

Edukt 1

HCID 5311101Fluticasone

Produkt 1

HCID 444036Fluticasone PropionateAusbeute 155,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The fluticasone (4.66 kg) obtained as above is dissolved in mixture of methanol (45 lit) and dichloromethane (45 lit) under stirring at ambient temperature and charcoalized. The methylene chloride is recovered (by distillation) by distillation at atmospheric pressure. The mixture is then gradually cooled to 10° C. and stirred for 60 min. The crystallized product is filtered, washed with methanol (4.5 lit) and dried at 55–60° C. to obtain pure fluticasone propionate (Yield 4.09 kg, overall yield 84.51%, purity 99.37%).

Aufarbeitung

  1. customThe methylene chloride is recovered
  2. distillation(by distillation)
  3. distillationby distillation at atmospheric pressure
  4. temperatureThe mixture is then gradually cooled to 10° C.
  5. stirringstirred for 60 min
  6. filtrationThe crystallized product is filtered
  7. washwashed with methanol (4.5 lit)
  8. customdried at 55–60° C.

Quellen und Nachweise

ORD-Eintrag
ord-e7f874c5d0ed44289fc50c03bf3e8939
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208613B2

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