Potassium Hydroxide → Dehydrolithocholic Acid

HRID 481116

反応式

HRID 481116 の反応式
[O:1]=[C:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH:13]=[CH:14][C:15]([O:17]CC)=[O:16])=[CH:3]1.[OH-].[K+]>C(O)C.[Pd]>[O:1]=[C:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 69537717Ethyl 3-oxo-4,22-choladienate

生成物 1

HCID 5283906Dehydrolithocholic Acid収率 93.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Ethyl 3-oxo-4,22-choladienate (2.39 g) was dissolved in 99% ethanol (170 ml) containing 0.9 g of potassium hydroxide. 10% Palladium on carbon containing 50% H2O (0.16 g) was added and the mixture was hydrogenated at room temperature and 1 atmosphere for about 3 hours (280 ml hydrogen was consumed). The catalyst was removed by filtration and water (20 ml) was added. After stirring for 3 days, acetic acid was added to pH 4, the solution was concentrated under reduced pressure to about 10 ml, and 20 ml of water was added. After stirring, the mixture crystallised. Filtration and washing with water gave 2.1 g of the title compound. 1H-NMR (CDCl3, 300 MHz), 0.67 (3H, s); 0.92 (3H, d); 1.00 (3H, s); 2.68 (1H, t).

後処理

  1. customwas hydrogenated at room temperature
  2. custom1 atmosphere for about 3 hours (280 ml hydrogen was consumed)
  3. customThe catalyst was removed by filtration and water (20 ml)
  4. additionwas added
  5. additionacetic acid was added to pH 4
  6. concentrationthe solution was concentrated under reduced pressure to about 10 ml, and 20 ml of water
  7. additionwas added
  8. stirringAfter stirring
  9. customthe mixture crystallised
  10. filtrationFiltration
  11. washwashing with water

出典と根拠

ORDレコード
ord-4b16d8a74799457fbfedd0cad585f53c
出典データセット
uspto-grants-2003_11
特許番号
US06653492B2

関連ノート

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