Cortisol → cortienic acid

HRID 1695541

Reaction equation

HRID 1695541 reaction equation
I(O)(O)(O)(O)(O)=[O:2].[OH:8][C@@H:9]1[C@H:25]2[C@@H:16]([CH2:17][CH2:18][C:19]3[C@:24]2([CH3:26])[CH2:23][CH2:22][C:21](=[O:27])[CH:20]=3)[C@H:15]2[C@@:11]([CH3:33])([C@@:12]([OH:32])([C:28](=[O:31])CO)[CH2:13][CH2:14]2)[CH2:10]1>O.C1COCC1.[OH-].[Na+]>[OH:8][C@@H:9]1[C@H:25]2[C@@H:16]([CH2:17][CH2:18][C:19]3[C@:24]2([CH3:26])[CH2:23][CH2:22][C:21](=[O:27])[CH:20]=3)[C@H:15]2[C@@:11]([CH3:33])([C@@:12]([OH:32])([C:28]([OH:2])=[O:31])[CH2:13][CH2:14]2)[CH2:10]1

Participants

6

Reactant 2

HCID 5754CortisolHCID 25289Orthoperiodic acid

Product 1

HCID 11382469cortienic acidYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of orthoperiodic acid (21.4 g, 94 mmol) in water (80 ml) was added to a solution of (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (Hydrocortisone, 17.0 g, 46.9 mmol) in THF (350 ml), and the reaction mixture was stirred at room temperature in an open flask for 2 hours. Then the mixture was poured onto ice. After the ice had molten, the mixture was extracted with ethyl acetate (3 times 150 ml). Evaporation of the solvent gave a white solid, which was dissolved in aqueous NaOH (1 M, 150 ml). The solution was washed with ethyl acetate, and acidified with conc. aqueous HCl. The precipitate formed was collected by filtration, and dried on the sinter overnight to afford the target compound as an off-white powder (15.51 g, 95%).

Workup

  1. additionThen the mixture was poured onto ice
  2. extractionthe mixture was extracted with ethyl acetate (3 times 150 ml)
  3. customEvaporation of the solvent
  4. customgave a white solid, which
  5. washThe solution was washed with ethyl acetate
  6. customThe precipitate formed
  7. filtrationwas collected by filtration
  8. customdried on the sinter overnight

Sources & evidence

ORD record
ord-bf9659f1d0df42fcb50558f13113df1e
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Linked notes

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