HCID 10575424, compound → HCID 86758554, compound

HRID 990582Notes

Reaction equation

HRID 990582 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][O:15][C:16](=[O:44])[CH2:17][CH2:18][C@H:19]([C@@H:21]1[C@:38]2([CH3:39])[C@H:24]([C@H:25]3[C@H:35]([CH2:36][C@@H:37]2[OH:40])[C@:33]2([CH3:34])[C@@H:28]([CH2:29][C@@H:30]([N:41]=[N+:42]=[N-:43])[CH2:31][CH2:32]2)[CH2:27][CH2:26]3)[CH2:23][CH2:22]1)[CH3:20].COC(=O)CC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](C[C@@H]2O)[C@]2(C)[C@@H](C[C@@H](N=[N+]=[N-])CC2)C[C@H]3O)CC1)C>CC(C)=O>[CH3:14][O:15][C:16](=[O:44])[CH2:17][CH2:18][C@H:19]([C@@H:21]1[C@:38]2([CH3:39])[C@H:24]([C@H:25]3[C@H:35]([CH2:36][C:37]2=[O:40])[C@:33]2([CH3:34])[C@@H:28]([CH2:29][C@@H:30]([N:41]=[N+:42]=[N-:43])[CH2:31][CH2:32]2)[CH2:27][CH2:26]3)[CH2:23][CH2:22]1)[CH3:20]

Participants

5

Reactant 3

HCID 10575424HCID 10575424, compoundHCID 86758555HCID 86758555, compoundHCID 131709961Jones' reagent

Product 1

HCID 86758554HCID 86758554, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

12.5 mL of Jones reagent (33.3 mmol Cr(VI)) are dropped into a solution of 17.8 g of (3β,5β,12α)-3-azido-12-hydroxycholan-24-oic acid methyl ester (41.1 mmol) (prepared analogously to the method described for (3β,5β,7α,12α)-3-azido-7,12-dihydroxycholan-24-oic acid methyl ester in WO-A-95/32741: example 5) in acetone (600 mL) in 90 min at room temperature. After 20 h the mixture is filtered and the solution is evaporated. The residue is dissolved in CHCl3 (400 mL) and the solution is washed with a NaHCO3 saturated aqueous solution then with H2O. The solution is dried and evaporated to give a crude which is crystallized from 96% EtOH to obtain 14.1 g of the desired product (32.9 mmol).

Workup

  1. customprepared analogously to the method
  2. customin 90 min
  3. customat room temperature
  4. filtrationAfter 20 h the mixture is filtered
  5. customthe solution is evaporated
  6. dissolutionThe residue is dissolved in CHCl3 (400 mL)
  7. washthe solution is washed with a NaHCO3 saturated aqueous solution
  8. customThe solution is dried
  9. customevaporated
  10. customto give a crude which
  11. customis crystallized from 96% EtOH

Sources & evidence

ORD record
ord-f1eaf6f3b72441ff9e7add79c0db7590
Source dataset
uspto-grants-2002_10
Patent number
US06461588B1

Reaction notes

Loading…