4-Toluenesulfonyl chloride → 20-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene

HRID 1587608Notes

Reaction equation

HRID 1587608 reaction equation
[CH3:1][CH:2]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([O:29][C:30]([O:32][CH3:33])=[O:31])[CH2:15][C@@H:16]2[O:24][C:25]([O:27][CH3:28])=[O:26])=[CH:11][CH:10]=3)[CH2:7][CH2:6]1)[CH2:3][OH:4].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>N1C=CC=CC=1>[CH3:1][CH:2]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([O:29][C:30]([O:32][CH3:33])=[O:31])[CH2:15][C@@H:16]2[O:24][C:25]([O:27][CH3:28])=[O:26])=[CH:11][CH:10]=3)[CH2:7][CH2:6]1)[CH2:3][O:4][S:40]([C:37]1[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=1)(=[O:42])=[O:41]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6778866020-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)pregna-5,7-dien-21-ol

Product 1

HCID 8674694320-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-dieneYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 1 ml of pyridine was dissolved 81 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)pregna-5,7-dien-21 -ol and, then, under ice-cooling, 70 mg of p-toluenesulfonyl chloride was added. The mixture was stirred at that temperature for 3 hours. The reaction mixture was then poured into ice water and extracted with diethyl ether. The extract was serially washed with aqueous copper sulfate solution, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 79 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with diethyl ether
  3. washThe extract was serially washed with aqueous copper sulfate solution, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7c08e8ae65a4b908ed6ab34553790d3
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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