Reaction #502086

ord-ae05c6e12d1f40a1be49aa744b0431b9

Reaction equation

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2
→
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulonic acid

Reactants

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2

Reagents

None

Solvents

O
water
—
NaH2PO4.H2O
CC#N.O
CH3CN—H2O

Conditions

Temperature
2.5°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture warmed to room temperature
  2. 2
    OtherThe reaction is quenched by addition of Na2S2O5 (380 mg)
  3. 3
    Extractionextracted with ethyl acetate
  4. 4
    ExtractionThe organic extract
  5. 5
    Washis washed with water and brine
  6. 6
    Dryingdried (Na2SO4)
  7. 7
    Filtrationfiltered
  8. 8
    Concentrationconcentrated

Procedure

The betulone aldehyde prepared from the last step is dissolved in a mixture of NaH2PO4.H2O (877 mg) and CH3CN—H2O (17 mL) and the suspension cooled to 0-5° C. 30% aqueous H2O2 (220 μL) and a solution of NaClO2 (200 mg) in water (16 mL) are then successively added, the mixture warmed to room temperature and stirred at this temperature for 1 h. The reaction is quenched by addition of Na2S2O5 (380 mg), and extracted with ethyl acetate. The organic extract is washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue is then subjected to column chromatography to afford betulonic acid (550 mg) as white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088757B2uspto-grants-2012_01