2-Iodoxybenzoic acid → Cortisone Acetate

HRID 1721532Notes

Reaction equation

HRID 1721532 reaction equation
[C:1]([O:4][CH2:5][CH:6]([OH:29])[C@:7]1([OH:28])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C:22](=[O:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[CH3:2][C:1]([O:4][CH2:5][C:6]([C@:7]1([OH:28])[C@@:24]2([CH3:25])[CH2:23][C:22]([C@@H:21]3[C@:19]4([CH3:20])[C:14](=[CH:15][C:16]([CH2:17][CH2:18]4)=[O:27])[CH2:13][CH2:12][C@H:11]3[C@@H:10]2[CH2:9][CH2:8]1)=[O:26])=[O:29])=[O:3]

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 10927596HCID 10927596, compound

Product 1

HCID 5745Cortisone AcetateYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 21-acetoxy-17,20-dihydroxy-pregn-4-en-3,11-dione (730 mg, 1.81 mmol) and o-iodoxybenzoic acid I (1 g, 3.57 mmol) in DMSO (7 ml) was stirred at 50° C. for 3 h. The solution was then diluted with water (10 ml), stirred for 10 min, filtered and extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The organic solvent was distilled under vacuum. The residue was crystallised from ethanol to give 676 mg (93%) of cortisone acetate, mp 238°-240° C. (lit. 238°-240° C.)

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. distillationThe organic solvent was distilled under vacuum
  6. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-bf8d308aa8594aef9154c7fe5ab941e3
Source dataset
uspto-grants-1996_04
Patent number
US05510538

Reaction notes

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