Reaction #92999

ord-8ad86bbd00414540bc192105b311a358

Reaction equation

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
Yield 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
Yield 56.2%

Reactants

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

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US04609650uspto-grants-1986_09