Sulfuric Acid → 16beta-Ethyl-17beta-(3-carboxypropyl)carbonyloxyacetoxy-4-estren-3-one

HRID 64721

반응식

HRID 64721 반응식
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][OH:25])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[C:27]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28]1.C(N(CC)CC)C.S(=O)(=O)(O)O>CN(C)C=O>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:25][C:27]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:34])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 7046644116beta-Ethyl-17beta-glycoloyloxy-4-estren-3-one

생성물 1

HCID 7046754216beta-Ethyl-17beta-(3-carboxypropyl)carbonyloxyacetoxy-4-estren-3-one수율 56.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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.

후처리

  1. customto stand at room temperature
  2. custom(15°-25° C.)
  3. customfor 3 hours
  4. extractionfollowed by extraction with 100 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is then distilled off under reduced pressure
  9. washthe residue is subjected to column chromatography, elution
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent
  12. customgiving a colorless oil, which

출처 및 근거

ORD 기록
ord-8ad86bbd00414540bc192105b311a358
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609650

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