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

HRID 64721

反応式

HRID 64721 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ad86bbd00414540bc192105b311a358
出典データセット
uspto-grants-1986_09
特許番号
US04609650

関連ノート

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