Methane → Beclomethasone dipropionate n-hexane

HRID 28106Notes

Reaction equation

HRID 28106 reaction equation
[CH3:1][CH2:2][C:3]([O:5][CH2:6][C:7]([C@:9]1([O:32][C:33]([CH2:35][CH3:36])=[O:34])[C@@:13]2([CH3:30])[CH2:14][C@H:15]([OH:29])[C@:16]3([Cl:28])[C@:26]4([CH3:27])[C:20](=[CH:21][C:22]([CH:24]=[CH:25]4)=[O:23])[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][C@@H:10]1[CH3:31])=[O:8])=[O:4].C>C(Cl)Cl>[CH3:1][CH2:2][C:3]([O:5][CH2:6][C:7]([C@:9]1([O:32][C:33]([CH2:35][CH3:36])=[O:34])[C@@:13]2([CH3:30])[CH2:14][C@H:15]([OH:29])[C@:16]3([Cl:28])[C@:26]4([CH3:27])[C:20](=[CH:21][C:22]([CH:24]=[CH:25]4)=[O:23])[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][C@@H:10]1[CH3:31])=[O:8])=[O:4].[CH3:6][CH2:7][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 297MethaneHCID 21700Beclomethasone Dipropionate

Product 1

HCID 70194159Beclomethasone dipropionate n-hexane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 300 g of beclomethasone dipropionate in 2 liters of methylene chloride at reflux. Treat with 15 g activated charcoal for 15 minutes at reflux and filter while hot. Concentrate the filtered solution to a volume of 900 ml and while maintaining reflux add slowly 900 ml of n-hexane. Cool to 0-10° C. Filter the resultant precipitate and wash with n-hexane. Dry the precipitate in air at <50° C. until constant weight to afford beclomethasone dipropionate-n-hexane solvate having an [α]/D25 =+85.5±2° in dioxane and an ε1% (extinction coefficient) in 1% solution=275±10 at 239 mu. Analysis by gas chromatography shows an n-hexane content of 4.6%. The beclomethasone dipropionate content (determined by ultraviolet assay) is 94.5%.

Workup

  1. temperatureat reflux
  2. additionTreat with 15 g
  3. customfor 15 minutes
  4. temperatureat reflux
  5. filtrationfilter while hot
  6. concentrationConcentrate the filtered solution to a volume of 900 ml
  7. temperaturewhile maintaining
  8. temperaturereflux
  9. additionadd slowly 900 ml of n-hexane
  10. filtrationFilter the resultant precipitate
  11. washwash with n-hexane
  12. customDry the precipitate in air at <50° C. until constant weight

Sources & evidence

ORD record
ord-6bca53e7e65b47d685cb4bcb13ec6c13
Source dataset
uspto-grants-1980_09
Patent number
US04225597

Reaction notes

Loading…