Cortisol → Hydrocortisone (4-chloro)butanoate

HRID 1271024Notes

Reaction equation

HRID 1271024 reaction equation
[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]

Participants

5

Reactant 3

HCID 5754CortisolHCID 8471TriethylamineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 86595714Hydrocortisone (4-chloro)butanoateYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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.

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)
  5. customto give a white solid with a 53% yield by weight, which
  6. customa melting point (m.p.) of 155° C.

Sources & evidence

ORD record
ord-fb52b164b4f44c2c8b347e80e41fe0e9
Source dataset
uspto-grants-2007_04
Patent number
US07205288B2

Reaction notes

Loading…