Sodium Bicarbonate → HCID 53832674, compound

HRID 1105589Notes

Reaction equation

HRID 1105589 reaction equation
C(=O)(O)[O-].[Na+].C(O)(=O)C.C(O)(=O)C.[OH:14][CH2:15][C@@:16]12[C@@H:36]3[C@H:24]([C@H:25]4[C@:33]([CH3:37])([CH2:34][CH2:35]3)[C@@H:28]([C:29](=[O:32])[CH2:30][OH:31])[CH2:27][CH2:26]4)[CH:23]=[CH:22][C:21]1=[CH:20][C:19](=[O:38])[CH2:18][CH2:17]2>O.CO>[OH:14][CH2:15][C@@:16]12[C@@H:36]3[C@H:24]([C@H:25]4[C@:33]([CH3:37])([CH2:34][CH2:35]3)[C@@H:28]([C:29](=[O:32])[CH2:30][OH:31])[CH2:27][CH2:26]4)[CH:23]=[CH:22][C:21]1=[CH:20][C:19](=[O:38])[CH2:18][CH2:17]2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86738188HCID 86738188, compound

Product 1

HCID 53832674HCID 53832674, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 211 mg of sodium bicarbonate in 2.6 ml of water is added to a solution of 100 mg of 19,21-dihydroxypregna-4,6-diene-3,20-dione diacetate in 6.5 ml of methanol and the mixture is heated under reflux for 3 hours and concentrated in vacuo. A solution of the residue in methylene chloride is washed with a 15% aqueous sodium chloride solution, dried with sodium sulphate and concentrated in vacuo. The residue is taken up in a mixture of hexane and ethyl acetate (1:1) and chromatographed over silica gel. After evaporating off the solvent, the product is dissolved and allowed to crystallise from methylene chloride/diethyl ether/diisopropyl ether, yielding 19,21-dihydroxypregna-4,6-diene-3,20-dione, melting point: 161°-164°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. washA solution of the residue in methylene chloride is washed with a 15% aqueous sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated in vacuo
  7. additionThe residue is taken up in a mixture of hexane and ethyl acetate (1:1)
  8. customchromatographed over silica gel
  9. customAfter evaporating off the solvent
  10. dissolutionthe product is dissolved
  11. customto crystallise from methylene chloride/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-1909e9e64cb94575a5fd7080ceb8669e
Source dataset
uspto-grants-1982_01
Patent number
US04309423

Reaction notes

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