반응 #92999

ord-8ad86bbd00414540bc192105b311a358

반응 방정식

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
수율 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
수율 56.2%

반응물

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

시약

없음

용매

CN(C)C=O
dimethylformamide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04609650uspto-grants-1986_09