Sodium Iodide → 21-Iodo-20-methyl-1alpha,3beta-bis(methoxycarbonyloxy)-pregna-5,7-diene

HRID 1587633Notes

Reaction equation

HRID 1587633 reaction equation
[CH3:1][CH:2]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:39][C:40]([O:42][CH3:43])=[O:41])[CH2:25][C@@H:26]2[O:34][C:35]([O:37][CH3:38])=[O:36])=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[I-:44].[Na+]>CC(C)=O>[I:44][CH2:3][CH:2]([CH3:1])[C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:39][C:40]([O:42][CH3:43])=[O:41])[CH2:25][C@@H:26]2[O:34][C:35]([O:37][CH3:38])=[O:36])=[CH:21][CH:20]=3)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 8674694320-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene

Product 1

HCID 6778826821-Iodo-20-methyl-1alpha,3beta-bis(methoxycarbonyloxy)-pregna-5,7-dieneYield 77.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 53 mg of 20-methyl-1α,3β-bis-(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7 -diene in 5 ml of acetone was added 120 mg of sodium iodide and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled, then the acetone was distilled off under reduced pressure, water was added to the residue, and the resulting mixture was extracted with diethyl ether. The extract was washed with water, an aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried over sodium sulfate and concentrated. Purification of the residue by silica gel column chromatography gave 38 mg of 21-iodo-20-methyl-1α,3β-bis(methoxycarbonyloxy)-pregna-5,7-diene.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. distillationthe acetone was distilled off under reduced pressure, water
  5. additionwas added to the residue
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialan aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried over sodium sulfate
  9. concentrationconcentrated
  10. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-cd9e82362a1c422cb0615f4bd257cc6f
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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