Réaction #92997

ord-ba43561350ab4dbdae794445f8174128

Équation de réaction

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
O=C([O-])CCC(=O)O.[Na+]
monosodium succinate
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC(=O)O
above-identified compound
Rendement 24.5%
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC(=O)O
16β-Ethyl-17β-(2-carboxyethyl)carbonyloxyacetoxy-4-estren-3-one
Rendement 24.5%

Réactifs

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
O=C([O-])CCC(=O)O.[Na+]
monosodium succinate

Réactifs

Aucun

Solvants

CC(C)=O
acetone

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  2. 2
    Extractionthe residue is extracted with 150 ml of ethyl acetate
  3. 3
    AutreThe organic layer is separated
  4. 4
    Lavagewashed with water and saturated aqueous sodium chloride solution
  5. 5
    Séchagedried over anhydrous sodium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Lavagepassage of 450 ml of chloroform, elution
  8. 8
    AutreThe eluate is evaporated under reduced pressure
  9. 9
    Autreto remove the solvent
  10. 10
    Autregiving colorless crystals
  11. 11
    LavageThe product is washed with petroleum ether
  12. 12
    Autredried

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04609650uspto-grants-1986_09