Perchloric Acid → (11β,16β)-11-Chloro-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione

HRID 1580571Notes

Reaction equation

HRID 1580571 reaction equation
C([O:4][CH2:5][C:6](=[O:30])[C@:7]1([OH:29])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([Cl:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][C@@H:8]1[CH3:28])(=O)C.Cl(O)(=O)(=O)=O.C([O-])(=O)C.[Na+]>CO>[Cl:26][C@H:22]1[CH2:23][C@@:24]2([CH3:25])[C@@H:10]([CH2:9][C@H:8]([CH3:28])[C@:7]2([OH:29])[C:6](=[O:30])[CH2:5][OH:4])[C@H:11]2[C@H:21]1[C@:19]1([CH3:20])[C:14]([CH2:13][CH2:12]2)=[CH:15][C:16](=[O:27])[CH:17]=[CH:18]1

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 517045Sodium AcetateHCID 68131640HCID 68131640, compound

Product 1

HCID 18595305(11β,16β)-11-Chloro-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 21-acetoxy-11β-chloro-17-hydroxy-16β-methylpregna-1,4-diene-3,20-dione (100 mg.) in methanol (7 ml.) was treated with 60% aqueous perchloric acid (0.2 ml.) at room temperature. After 24 hours sodium acetate (100 mg.) was added and about half of the solvent was evaporated in vacuo. Purification of the remaining solution by preparative thin layer chromatography and crystallisation from methanol afforded 11β-chloro-17,21-dihyroxy-16β-methylpregna-1,4-diene-3,20-dione as needles, m.p. 202°-204° decomp (Kofler).

Workup

  1. customwas evaporated in vacuo
  2. customPurification of the remaining solution
  3. customby preparative thin layer chromatography and crystallisation from methanol

Sources & evidence

ORD record
ord-707dc62269d64f509bc4904f2d988b2f
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

Loading…