Cortisol → Hydrocortisone (4-chloro)butanoate

HRID 397301

Reaktionsgleichung

Reaktionsgleichung von HRID 397301
[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]

Komponenten

5

Edukt 3

HCID 5754CortisolHCID 8471TriethylamineHCID 783704-Chlorobutyryl chloride

Produkt 1

HCID 86595714Hydrocortisone (4-chloro)butanoateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-01127625807d4126ba9a0a5612202df9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610676B1

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