Dimethyl Sulfoxide → HCID 14695740, compound

HRID 2231995Notes

Reaction equation

HRID 2231995 reaction equation
[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[O:18][CH2:19]2)[C@H:14]2O[C@@H:13]32)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].[FH:29].[K].CS(C)=O>O>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[O:18][CH2:19]2)[C:14]([F:29])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14695738HCID 14695738, compoundHCID 53443437Potassium fluoride, 99%, spray-dried

Product 1

HCID 14695740HCID 14695740, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 100 mg of 17α-acetoxy-6α,7α-epoxy-2-oxa-4-pregnene-3,20-dione, 200 mg of potassium hydrogen fluoride and 1 ml of dimethyl sulfoxide was heated at 140° C. for 20 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by TLC [developing solvent: chloroform/acetone (50/1)] to give 20 mg of 17α-acetoxy-6-fluoro-2-oxapregna-4,6-diene-3,20-dione.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by TLC [developing solvent: chloroform/acetone (50/1)]

Sources & evidence

ORD record
ord-e6bb9d072b864c27b786b9ee74016bcb
Source dataset
uspto-grants-1988_11
Patent number
US04785103

Reaction notes

Loading…