Cortisol → Cortienic acid

HRID 2197395Notes

Reaction equation

HRID 2197395 reaction equation
[OH:1][C@@H:2]1[C@H:18]2[C@@H:9]([CH2:10][CH2:11][C:12]3[C@:17]2([CH3:19])[CH2:16][CH2:15][C:14](=[O:20])[CH:13]=3)[C@H:8]2[C@@:4]([CH3:26])([C@@:5]([OH:25])([C:21](=[O:24])CO)[CH2:6][CH2:7]2)[CH2:3]1.I(O)(O)(O)(O)(O)=[O:28]>CO.O>[OH:1][C@@H:2]1[C@H:18]2[C@@H:9]([CH2:10][CH2:11][C:12]3[C@:17]2([CH3:19])[CH2:16][CH2:15][C:14](=[O:20])[CH:13]=3)[C@H:8]2[C@@:4]([CH3:26])([C@@:5]([OH:25])([C:21]([OH:28])=[O:24])[CH2:6][CH2:7]2)[CH2:3]1

Participants

5

Reactant 2

HCID 5754CortisolHCID 25289Orthoperiodic acid2×

Product 1

HCID 11382469Cortienic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 1000 mL round-bottomed flask was suspended (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 (10.4 g, 28.69 mmol) in MeOH (200 mL) and a solution of orthoperiodic acid (9.81 g, 43.04 mmol) in water (200 mL) was added to give a colorless solution. The mixture was stirred for 45 minutes after which an additional 3 g of orthoperiodic acid was added and stirring was continued for another hour. MeOH was removed in vacuo and the residual aqueous mixture was diluted with 200 ml of water. The resulting solid was isolated by filtration and was air-dried on the sinter to yield 8.1 g of the desired compound as a white solid. APCI-MS m/z: 349 [MH+].

Workup

  1. customIn a 1000 mL round-bottomed flask was suspended
  2. customto give a colorless solution
  3. additionwas added
  4. waitwas continued for another hour
  5. customMeOH was removed in vacuo
  6. additionthe residual aqueous mixture was diluted with 200 ml of water
  7. customThe resulting solid was isolated by filtration
  8. customwas air-dried on the sinter

Sources & evidence

ORD record
ord-3843de7fdf97437eba2b6f6eb78e8250
Source dataset
uspto-grants-2012_12
Patent number
US08338587B2

Reaction notes

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