Methanol → Chenodeoxycholic Acid

HRID 2199017ノート

反応式

HRID 2199017 の反応式
CO.[OH-].[K+].C([O:8][C@@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:11]([CH2:12][C@@H:13]([O:36]C(=O)C)[C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH2:10]1)(=O)C>C(O)(C)C>[CH3:26][C@@H:19]([C@@H:18]1[C@@:27]2([CH3:35])[CH2:28][CH2:29][C@@H:30]3[C@@:31]4([CH3:34])[CH2:32][CH2:33][C@@H:9]([OH:8])[CH2:10][C@H:11]4[CH2:12][C@@H:13]([OH:36])[C@H:14]3[C@@H:15]2[CH2:16][CH2:17]1)[CH2:20][CH2:21][C:22]([OH:24])=[O:23]

参加物

5

反応物 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 11466003Chenodeoxycholic acid diacetate methyl ester

生成物 1

HCID 10133Chenodeoxycholic Acid収率 69.3%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a solution of 3 ml of methanol, 5 ml of isopropanol and 0.8 g of potassium hydroxide was added 0.294 g (0.000599 mol) of methyl 3α,7α-diacetyloxy-5β-cholan-24-oate. The mixture was heated to reflux under an argon atmosphere for 4 hr. then stirred overnight at room temperature. The solvents were removed in vacuo. The mixture was acidified with 1 N HCl and extracted with 3×25 ml of ethyl acetate. The combined ethyl acetate extracts were washed with water then dried over anhydrous sodium sulfate. The mixture was filtered and solvents removed in vacuo. The residue were recrystallized from ethyl acetate to give 0.163 g (69.3%) of chenodeoxycholic acid, mp 117°-118° C., which did not depress when mixed with authentic material (mp 117°-118° C. from ethyl acetate).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux under an argon atmosphere for 4 hr
  3. customThe solvents were removed in vacuo
  4. extractionextracted with 3×25 ml of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with water
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. filtrationThe mixture was filtered
  8. customsolvents removed in vacuo
  9. customThe residue were recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-0d6f9aefa3fb4505af7c0c11c2748644
出典データセット
uspto-grants-1982_11
特許番号
US04360470

反応ノート

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