Fluticasone → Fluticasone Propionate

HRID 1272567Notes

Reaction equation

HRID 1272567 reaction equation
[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]

Participants

4

Reactant 1

HCID 5311101Fluticasone

Product 1

HCID 444036Fluticasone PropionateYield 155.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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.

Sources & evidence

ORD record
ord-e7f874c5d0ed44289fc50c03bf3e8939
Source dataset
uspto-grants-2007_04
Patent number
US07208613B2

Reaction notes

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