Pyridine → Osaterone acetate

HRID 2231991Notes

Reaction equation

HRID 2231991 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]([Cl:28])[C@H:13]3O)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.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]([Cl:28])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 14695734HCID 14695734, compound

Product 1

HCID 114992Osaterone acetateYield 77.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 70 mg of 17α-acetoxy-6β-chloro-7α-hydroxy-2-oxa-4-pregnene-3,20-dione, 400 mg of p-toluenesulfonyl chloride, 1 ml of 4-dimethylaminopyridine and 0.9 ml of pyridine was heated under reflux for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 50% hydrochloric acid and then 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 (19/1)] to give 52 mg of 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione. The 1H-NMR spectrum of this compound was the same as that of the compound produced in Example 1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with 50% hydrochloric acid
  5. dry with materialwith a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)]

Sources & evidence

ORD record
ord-d1891d46dbcc4404987c165b02e72123
Source dataset
uspto-grants-1988_11
Patent number
US04785103

Reaction notes

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