Hydrochloric Acid → Osaterone acetate

HRID 2231990Notes

Reaction equation

HRID 2231990 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-720f70482f734dc18fb4ff5542ab316a
Source dataset
uspto-grants-1988_11
Patent number
US04785103

Reaction notes

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