Cortisol → 11beta-Hydroxyandrost-4-ene-3,17-dione

HRID 80415

反応式

HRID 80415 の反応式
[CH3:1][C@@:2]12[C@H:12]3[C@@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])(C(CO)=O)[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[O-][Bi](=O)=O.[Na+]>C(O)(=O)C>[OH:26][C@H:13]1[CH2:14][C@@:15]2([CH3:25])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:24])[C@H:11]2[C@H:12]1[C@:2]1([CH3:1])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]1

参加物

4

反応物 2

HCID 5754CortisolHCID 4063671Sodium bismuthate

生成物 1

HCID 9414111beta-Hydroxyandrost-4-ene-3,17-dione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

11β-Hydroxy-4-androstene-3,17-dione was synthesised in a single stage, oxidative reaction from hydrocortisone. The starting material was dissolved in acetic acid and allowed to react with sodium bismuthate overnight in the dark. The mixture was then filtered and washed with dichloromethane. The organic phase was separated, washed with water and neutralised with sodium bicarbonate (to pH 8). The organic phase was again separated and then washed, dried and filtered. Finally, the organic solvent was removed under reduced pressure. Pure product was achieved by recrystallising from ethyl acetate/heptane.

後処理

  1. filtrationThe mixture was then filtered
  2. washwashed with dichloromethane
  3. customThe organic phase was separated
  4. washwashed with water and neutralised with sodium bicarbonate (to pH 8)
  5. customThe organic phase was again separated
  6. washwashed
  7. customdried
  8. filtrationfiltered
  9. customFinally, the organic solvent was removed under reduced pressure
  10. customby recrystallising from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-c893b0bf3df64b33afa12daa136006fc
出典データセット
uspto-grants-2014_09
特許番号
US08846652B2

関連ノート

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