Cortisol → Hydrocortisone (4-chloro)butanoate

HRID 2220819Notes

Reaction equation

HRID 2220819 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-9a0d65b8483649489b34cd2bb2fb0f20
Source dataset
uspto-grants-2008_05
Patent number
US07368442B2

Reaction notes

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