Reacción #92997

ord-ba43561350ab4dbdae794445f8174128

Ecuación de reacción

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
Rendimiento 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
Rendimiento 24.5%

Reactantes

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

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  2. 2
    Extracciónthe residue is extracted with 150 ml of ethyl acetate
  3. 3
    OtroThe organic layer is separated
  4. 4
    Lavadowashed with water and saturated aqueous sodium chloride solution
  5. 5
    Secadodried over anhydrous sodium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Lavadopassage of 450 ml of chloroform, elution
  8. 8
    OtroThe eluate is evaporated under reduced pressure
  9. 9
    Otroto remove the solvent
  10. 10
    Otrogiving colorless crystals
  11. 11
    LavadoThe product is washed with petroleum ether
  12. 12
    Otrodried

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04609650uspto-grants-1986_09