Methanol → Cortexolone Impurity A

HRID 1076282Notes

Reaction equation

HRID 1076282 reaction equation
[OH:1][CH2:2][C:3](=[O:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.CO.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[OH-].[Na+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[O:23]=[C:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:24])[CH:2]=[O:1])=[CH:12]1

Participants

7

Reactant 4

HCID 887Methanol2×HCID 6049Ethylenediaminetetraacetic AcidHCID 6166DeoxycorticosteroneHCID 14798Sodium Hydroxide

Product 1

HCID 331384Cortexolone Impurity A

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

1.0 g. of 21-hydroxy-4-pregnene-3,20-dione is dissolved in 125 ml. of methanol and combined with a solution of 250 mg. of copper(II) acetate in 125 ml. of methanol. For 30 minutes, air is passed through the solution, and the latter is then combined with a solution of 500 mg. of ethylenediaminetetraacetic acid in 50 ml. of water, adjusted to pH 9 with 1N sodium hydroxide solution. The mixture is concentrated under vacuum at 40° C. and extracted with ethyl acetate. The extract is dried over sodium sulfate and evaporated under vacuum. As the residue, 1.1 g. of 3,20-dioxo-4-pregnen-21-al is obtained as a viscous oil.

Workup

  1. concentrationThe mixture is concentrated under vacuum at 40° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract is dried over sodium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-6d73665ed9a441f2b32b64f4b7347125
Source dataset
uspto-grants-1976_05
Patent number
US03956347

Reaction notes

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