Cortisol → Hydrocortisone (4-chloro)butanoate

HRID 397301

反応式

HRID 397301 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].C(N(CC)CC)C.[CH3:15][C@@:16]12[C@H:26]3[C@@H:27]([OH:40])[CH2:28][C@:29]4([CH3:39])[C@@:33]([OH:38])([C:34]([CH2:36][OH:37])=[O:35])[CH2:32][CH2:31][C@H:30]4[C@@H:25]3[CH2:24][CH2:23][C:22]1=[CH:21][C:19](=[O:20])[CH2:18][CH2:17]2>C(Cl)(Cl)Cl>[CH3:15][C@@:16]12[C@H:26]3[C@@H:27]([OH:40])[CH2:28][C@:29]4([CH3:39])[C@@:33]([OH:38])([C:34]([CH2:36][OH:37])=[O:35])[CH2:32][CH2:31][C@H:30]4[C@@H:25]3[CH2:24][CH2:23][C:22]1=[CH:21][C:19](=[O:20])[CH2:18][CH2:17]2.[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([O-:6])=[O:20]

参加物

5

反応物 3

HCID 5754CortisolHCID 8471TriethylamineHCID 783704-Chlorobutyryl chloride

生成物 1

HCID 86595714Hydrocortisone (4-chloro)butanoate収率 53%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

4 portions of 4-chlorobutanoylchloride (0.32 ml×4) and triethylamine (0.3 g×4) were added in 24 hours to a solution of hydrocortisone (1 g) in CHCl3 dried over P2O5, and stirred for 3 days. The solution was treated with water, the organic phase was separated, dried (Na2SO4) and deprived of the solvent at reduced pressure. The crude residue was ground with hexane and CH2Cl2 to give a white solid with a 53% yield by weight, which had a melting point (m.p.) of 155° C.

後処理

  1. dry with materialdried over P2O5
  2. additionThe solution was treated with water
  3. customthe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customto give a white solid with a 53% yield by weight, which
  6. customa melting point (m.p.) of 155° C.

出典と根拠

ORDレコード
ord-01127625807d4126ba9a0a5612202df9
出典データセット
uspto-grants-2003_08
特許番号
US06610676B1

関連ノート

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