Réaction #92999

ord-8ad86bbd00414540bc192105b311a358

Équation de réaction

O=S(=O)(O)O
sulfuric acid
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
O=C1CCCC(=O)O1
glutaric anhydride
CCN(CC)CC
triethylamine
→
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)CCCC(=O)O
above-identified compound
Rendement 56.2%
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)CCCC(=O)O
16β-Ethyl-17β-(3-carboxypropyl)carbonyloxyacetoxy-4-estren-3-one
Rendement 56.2%

Réactifs

O=S(=O)(O)O
sulfuric acid
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
O=C1CCCC(=O)O1
glutaric anhydride
CCN(CC)CC
triethylamine

Réactifs

Aucun

Solvants

CN(C)C=O
dimethylformamide

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreto stand at room temperature
  2. 2
    Autre(15°-25° C.)
  3. 3
    Autrefor 3 hours
  4. 4
    Extractionfollowed by extraction with 100 ml of ethyl acetate
  5. 5
    AutreThe organic layer is separated
  6. 6
    Lavagewashed with water and saturated aqueous sodium chloride solution
  7. 7
    Séchagedried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    Lavagethe residue is subjected to column chromatography, elution
  10. 10
    AutreThe eluate is evaporated under reduced pressure
  11. 11
    Autreto remove the solvent
  12. 12
    Autregiving a colorless oil, which

Mode opératoire

In 10 ml of dimethylformamide is dissolved 0.5 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one, and 0.2 g of glutaric anhydride and then 0.3 ml of triethylamine are added to the above solution. The mixture is allowed to stand at room temperature (15°-25° C.) for 3 hours and poured into 20 ml of 10% aqueous sulfuric acid, followed by extraction with 100 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, elution being carried out with 200 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving a colorless oil, which is allowed to stand to give 0.37 g of the above-identified compound as a solid.

Source

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