تفاعل #92999

ord-8ad86bbd00414540bc192105b311a358

معادلة التفاعل

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
المردود 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
المردود 56.2%

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CN(C)C=O
dimethylformamide

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04609650uspto-grants-1986_09