Hydrogen Peroxide → 1alpha,3beta-Bis(methoxycarbonyloxy)-20-methyl-21-phenylsulfonylpregna-5,7-diene

HRID 1587632Notes

Reaction equation

HRID 1587632 reaction equation
[CH3:1][CH:2]([C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19]([CH2:20][C@@H:21]([O:36][C:37]([O:39][CH3:40])=[O:38])[CH2:22][C@@H:23]2[O:31][C:32]([O:34][CH3:35])=[O:33])=[CH:18][CH:17]=3)[CH2:14][CH2:13]1)[CH2:3][S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH:41]O>CO.O>[CH3:1][CH:2]([C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19]([CH2:20][C@@H:21]([O:36][C:37]([O:39][CH3:40])=[O:38])[CH2:22][C@@H:23]2[O:31][C:32]([O:34][CH3:35])=[O:33])=[CH:18][CH:17]=3)[CH2:14][CH2:13]1)[CH2:3][S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:41])=[O:5]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 6778888420-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7-diene

Product 1

HCID 541055811alpha,3beta-Bis(methoxycarbonyloxy)-20-methyl-21-phenylsulfonylpregna-5,7-diene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 29 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7-diene in 1 ml of methanol was added 0.5 ml of a 30% aqueous solution of hydrogen peroxide and the mixture was stirred at ambient temperature for 6 hours. The reaction mixture was diluted with water and the methanol was distilled off under reduced pressure. The residue was extracted with methylene chloride, the extract was washed with an aqueous solution of sodium thiosulfate, water and an aqueous solution of sodium chloride, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 13 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylsulfonylpregna-5,7-diene, whose 1H NMR spectrum was identical with that obtained in Example 5.

Workup

  1. distillationthe methanol was distilled off under reduced pressure
  2. extractionThe residue was extracted with methylene chloride
  3. washthe extract was washed with an aqueous solution of sodium thiosulfate, water
  4. dry with materialan aqueous solution of sodium chloride, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f08bab8f4539484f8b770e89193a0349
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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