2-Methylbutanoic Acid → 16beta-Ethyl-17beta-(2-methylbutyryl)oxyacetoxy-4-estren-3-one

HRID 64725

Reaction equation

HRID 64725 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].C(OCC)(=O)C.[CH3:33][CH:34]([CH2:38][CH3:39])[C:35]([OH:37])=[O:36]>CC(C)=O.[OH-].[Na+].O>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:37][C:35](=[O:36])[CH:34]([CH3:33])[CH2:38][CH3:39])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

7

Reactant 3

HCID 83142-Methylbutanoic AcidHCID 8857Ethyl AcetateHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046791616beta-Ethyl-17beta-(2-methylbutyryl)oxyacetoxy-4-estren-3-one

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 30 ml of acetone is dissolved 0.4 ml of 2-methylbutyric acid, and 2.0 ml of 2N-NaOH and 3 ml of water is added, followed by addition of 0.88 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 hours and allowed to stand at room temperature (15°-25° C.) for 2 days, followed by addition of 150 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 100 ml of diisopropyl ether-n-hexane (2:8), elution is carried out with 400 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.8 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 6 hours
  3. customto stand at room temperature
  4. custom(15°-25° C.)
  5. customfor 2 days
  6. customThe organic layer is separated
  7. washwashed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent is then distilled off under reduced pressure
  10. washpassage of 100 ml of diisopropyl ether-n-hexane (2:8), elution
  11. additionis carried out with 400 ml of a 1:1 mixture of the same solvents
  12. customThe eluate is evaporated under reduced pressure
  13. customto remove the solvent

Sources & evidence

ORD record
ord-361e017f28494fbb8b46ffc7156fc566
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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