Water → HCID 86757977, compound

HRID 843208Notes

Reaction equation

HRID 843208 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:15][C@H:16]1[C@@:38]2([CH3:39])[C:28](=[CH:29][CH2:30][C@@H:31]2[C:32]2([O:37][CH2:36][CH2:35][O:34]2)[CH3:33])[C@H:27]2[C@@H:18]([C@:19]3([CH3:41])[C:24](=[CH:25][CH2:26]2)[CH2:23][C@@H:22]([OH:40])[CH2:21][CH2:20]3)[CH2:17]1)(=[O:14])[CH3:13].O>N1C=CC=CC=1>[C:12]([O:15][C@H:16]1[C@@:38]2([CH3:39])[C:28](=[CH:29][CH2:30][C@@H:31]2[C:32]2([O:37][CH2:36][CH2:35][O:34]2)[CH3:33])[C@H:27]2[C@@H:18]([C@:19]3([CH3:41])[C:24](=[CH:25][CH2:26]2)[CH2:23][C@@H:22]([O:40][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:21][CH2:20]3)[CH2:17]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21077894HCID 21077894, compound

Product 1

HCID 86757977HCID 86757977, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of p-toluenesulphonyl chloride (650 mg, 3.4 mmol) in pyridine (10 ml) was added dropwise to a mixture of the 20,20-Ethylenedioxypregna-5,14-diene-3β,12β-diol 12-acetate (22) (1.3 g, 3.1 mmol) in pyridine (15 ml) at 0° C. The reaction mixture was left stirring at room temperature for 24 hours after which water was added to the reaction mixture. The solution was extracted with ethyl acetate (2×50 ml), the ethyl acetate layer was washed citric acid (5×50 ml), saturated sodium bicarbonate solution (100 ml), saturated sodium chloride solution (100 ml) and water (100 ml) The ethyl acetate was dried (MgSO4), filtered, and evaporated and purified by flash column chromatography using hexane-ethyl acetate (8:2 v/v) as the eluant to give the β-O-tosyl steroid (26), (1.5 g, 84%), as a yellow oil, (Found M 570.271, C32H42O7S requires: M 570.273).

Workup

  1. waitThe reaction mixture was left
  2. additionwas added to the reaction mixture
  3. extractionThe solution was extracted with ethyl acetate (2×50 ml)
  4. washthe ethyl acetate layer was washed citric acid (5×50 ml), saturated sodium bicarbonate solution (100 ml), saturated sodium chloride solution (100 ml) and water (100 ml) The ethyl acetate
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-d96fbc8f47ed4bc8aea062a5f007e151
Source dataset
uspto-grants-2002_04
Patent number
US06376657B1

Reaction notes

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