Potassium Hydroxide → Anecortave

HRID 247540

Reaction equation

HRID 247540 reaction equation
C([O:4][CH2:5][C:6](=[O:28])[C@:7]1([OH:27])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=O)C.[OH-].[K+]>CO.C(Cl)Cl>[OH:27][C@:7]1([C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[C:6](=[O:28])[CH2:5][OH:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 111332Anecortave Acetate

Product 1

HCID 7074810AnecortaveYield 89.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1.5 g of 21-acetoxy-17-hydroxy-4,9(11)-pregnadiene-3,20-dione in 40 ml of methanol is agitated for 2 hours at room temperature with 15 ml of 0.2N methanolic potassium hydroxide solution. The reaction mixture is introduced into ice water. The precipitated product is suctioned off, dissolved in methylene chloride, washed with water, and dried over sodium sulfate, thus obtaining 1.2 g of 17,21-dihydroxy-4,9(11)-pregnadiene-3,20-dione; mp 248.2° C.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-7dcadc539d5c4a489db617cf82375914
Source dataset
uspto-grants-1987_11
Patent number
US04708823

Linked notes

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