Water → 20-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylthiopregna-5, 7-diene

HRID 1587609Notes

Reaction equation

HRID 1587609 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Br[CH2:11][CH:12]([CH3:42])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([O:37][C:38]([O:40][CH3:41])=[O:39])[CH2:23][C@@H:24]2[O:32][C:33]([O:35][CH3:36])=[O:34])=[CH:19][CH:18]=3)[CH2:15][CH2:14]1.O>CS(C)=O>[CH3:42][CH:12]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([O:37][C:38]([O:40][CH3:41])=[O:39])[CH2:23][C@@H:24]2[O:32][C:33]([O:35][CH3:36])=[O:34])=[CH:19][CH:18]=3)[CH2:15][CH2:14]1)[CH2:11][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 6778853721-Bromo-20-methyl-1alpha,3beta-bis(methoxycarbonyloxy)pregna-5,7-diene

Product 1

HCID 6778822120-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylthiopregna-5, 7-dieneYield 68.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 2 ml of dimethyl sulfoxide under ice-cooling, 55 mg of thiophenol and 20 mg of sodium hydroxide were stirred. Then, 54 mg of 21-bromo-20-methyl-1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene was added and the mixture was further stirred at ambient temperature for 3 hours. The reaction mixture was then poured into water and extracted with diethyl ether. The extract was washed with water and aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 39 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylthiopregna-5, 7-diene.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f7a1aca40e344d098c03506e08baae2
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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