Hydrochloric Acid → Osaterone acetate

HRID 2072893Notes

Reaction equation

HRID 2072893 reaction equation
[BH4-].[Na+].[C:3]([O:6][C@:7]1([C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[O:20][CH:21]2O)[C:16]([Cl:31])=[CH:15]3)[CH2:12][CH2:11]1)[C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4].C(=O)([O-])O.[Na+].Cl>O.CO>[C:3]([O:6][C@:7]1([C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[O:20][CH2:21]2)[C:16]([Cl:31])=[CH:15]3)[CH2:12][CH2:11]1)[C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 1378663717alpha-Acetoxy-6-chloro-1xi-hydroxy-2-oxapregna-4,6-diene-3,20-dione

Product 1

HCID 114992Osaterone acetateYield 62.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (72 mg) was added to a mixture of 200 mg of 17α-acetoxy-6-chloro-1ξ-hydroxy-2-oxapregna-4,6-diene-3,20-dione, 80 mg of sodium hydrogen carbonate, 20 ml of methanol and 10 ml of water, and the mixture was stirred at room temperature for 30 minutes. Concentrated hydrochloric acid (about 0.4 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The crude product was purified by TLC [developing solvent: chloroform)] to give 120 mg of 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe crude product was purified by TLC [

Sources & evidence

ORD record
ord-8f832c5a1c51409188cfebd0c133405e
Source dataset
uspto-grants-1990_04
Patent number
US04914106

Reaction notes

Loading…