Cortisol → Hydrocortisone 4-bromobutanoate

HRID 1371268Notes

Reaction equation

HRID 1371268 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].C(=O)([O-])[O-:9].[K+].[K+].[CH3:14][C@@:15]12[C@H:25]3[C@@H:26]([OH:39])[CH2:27][C@:28]4([CH3:38])[C@@:32]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:31][CH2:30][C@H:29]4[C@@H:24]3[CH2:23][CH2:22][C:21]1=[CH:20][C:18](=[O:19])[CH2:17][CH2:16]2>C(Cl)(Cl)Cl>[CH3:14][C@@:15]12[C@H:25]3[C@@H:26]([OH:39])[CH2:27][C@:28]4([CH3:38])[C@@:32]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:31][CH2:30][C@H:29]4[C@@H:24]3[CH2:23][CH2:22][C:21]1=[CH:20][C:18](=[O:19])[CH2:17][CH2:16]2.[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O-:6])=[O:9]

Participants

5

Reactant 3

HCID 5754CortisolHCID 11430Potassium CarbonateHCID 702254-Bromobutyryl chloride

Product 1

HCID 86606384Hydrocortisone 4-bromobutanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Five portions of 4-bromobutanoylchloride (0.35 ml×5) and potassium carbonate (0. 4 g×5) were added in 24 hours to a solution of hydrocortisone (1 g) in CHCl3 dried over P2O5 and stirred for 5 days. The solution was treated with water, the organic phase was separated, dried (Na2SO4) and deprived of the solvent at reduced pressure.

Workup

  1. dry with materialdried over P2O5
  2. additionThe solution was treated with water
  3. customthe organic phase was separated
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-55c54a5306444d8681b79dcd521d6d2d
Source dataset
uspto-grants-2007_01
Patent number
US07157450B2

Reaction notes

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