Reacción #92995

ord-b41cc64ac5c74bb4b545d671402d2dbb

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
CC(O)C(=O)[O-].[Na+]
sodium lactate
CCOC(C)=O
ethyl acetate
O
water
→
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)C(C)O
above-identified compound
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)C(C)O
16β-Ethyl-17β-lactoyloxyacetoxy-4-estren-3-one

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
CC(O)C(=O)[O-].[Na+]
sodium lactate
CCOC(C)=O
ethyl acetate
O
water

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONis added
  2. 2
    OtroThe organic layer is separated
  3. 3
    Lavadowashed with water and saturated aqueous sodium chloride
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  6. 6
    Lavadoin that order, elution
  7. 7
    OtroThe eluate is evaporated under reduced pressure
  8. 8
    Otroto remove the solvent

Procedimiento

In 30 ml of DMF is dissolved 3.4 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one, and 2.5 ml of 70% aqueous sodium lactate is added. The mixture is stirred at room temperature (15°-25° C.) for 3 hours and poured into a mixture of 350 ml of ethyl acetate and 30 ml of water. The organic layer is separated, washed with water and saturated aqueous sodium chloride 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 dichloromethane and 700 ml of diisopropyl ether in that order, elution is carried out with 1200 ml of diisopropyl ether-ethyl acetate (10:1). The eluate is evaporated under reduced pressure to remove the solvent, giving 3.0 g of the above-identified compound as a light yellow oil.

Fuente

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