Dimethyl Sulfoxide → Osaterone acetate

HRID 2231993Notes

Reaction equation

HRID 2231993 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]3OS(C)(=O)=O)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C([O-])(=O)C.[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]([Cl:28])=[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 517044Potassium AcetateHCID 14306878HCID 14306878, compound

Product 1

HCID 114992Osaterone acetateYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.35 g of 17α-acetoxy-6β-chloro-7α-mesyloxy-2-oxa-4-pregnene-3,20-dione, 0.83 g of potassium acetate and 0.88 ml of dimethyl sulfoxide was stirred at room temperature for 12 hours. Ice-cooled water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give 1.37 g 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. additionwas poured into the reaction mixture
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ac03e34c5a3248e188ea40808a73da74
Source dataset
uspto-grants-1988_11
Patent number
US04785103

Reaction notes

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