Methanol → Anecortave

HRID 1032030

Reaction equation

HRID 1032030 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.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

4

Reactant 2

HCID 887MethanolHCID 111332Anecortave Acetate

Product 1

HCID 7074810AnecortaveYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1.5 g of 21-acetoxy-17-hydroxy-4,9(11)-pregnadiene-3,20-dione in 40 ml is agitated for 2 hours at room temperature with 15 ml of methanol 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) pregnadiene3,20-dione; mp 248.2° C.

Workup

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

Sources & evidence

ORD record
ord-55c8034840ae47a2b610f62f85552da4
Source dataset
uspto-grants-1990_09
Patent number
US04956482

Linked notes

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