16beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one → 16beta-Ethyl-17beta-(2-carboxyethyl)carbonyloxyacetoxy-4-estren-3-one

HRID 64719Notes

Reaction equation

HRID 64719 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:27]([O-:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].[Na+]>CC(C)=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:32][C:30]([CH2:29][CH2:28][C:27]([OH:34])=[O:33])=[O:31])[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

4

Reactant 2

HCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-oneHCID 23690498Monosodium succinate

Product 1

HCID 7046746116beta-Ethyl-17beta-(2-carboxyethyl)carbonyloxyacetoxy-4-estren-3-oneYield 24.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 100 ml of 50% aqueous acetone are dissolved 1.5 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 0.7 g of monosodium succinate and the solution is stirred at room temperature (15°-25° C.) for 3 days. The acetone is distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 450 ml of chloroform, elution is carried out with 150 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving colorless crystals. The product is washed with petroleum ether and dried to give 0.4 g of the above-identified compound.

Workup

  1. distillationThe acetone is distilled off under reduced pressure
  2. extractionthe residue is extracted with 150 ml of ethyl acetate
  3. customThe organic layer is separated
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. washpassage of 450 ml of chloroform, elution
  8. customThe eluate is evaporated under reduced pressure
  9. customto remove the solvent
  10. customgiving colorless crystals
  11. washThe product is washed with petroleum ether
  12. customdried

Sources & evidence

ORD record
ord-ba43561350ab4dbdae794445f8174128
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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