Betulin → (+)-Betulonic acid

HRID 414902Notes

Reaction equation

HRID 414902 reaction equation
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].CC(C)=[O:35].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.C1C=CC=CC=1.CO>[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:31]([OH:35])=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C:16](=[O:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Participants

6

Reactant 2

HCID 72326BetulinHCID 131709961Jones' reagent

Product 1

HCID 122844(+)-Betulonic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

Starting off with Betulin (10 g) in acetone (300 mL), add freshly prepared Jones Reagent added dropwise at 0° C. Stir for 5 hours, quench with methanol (100 mL), then stir for 5 minutes and add H2O (200 mL). Remove organic solvent under vacuum, and then separate the precipitate by filtration. Wash precipitate on the filter with cooled water, and dry to obtain crude material. This dry material is to be dissolved in 30 mL benzene. The solution is then filtered through a layer of aluminum oxide and the eluate is treated with an aqueous 10% KOH solution until complete precipitation. The precipitate is then separated by filtration, washed with 10 mL cooled benzene, and dried to obtain white solid. The salt is dissolved in 30 mL methanol and the solution is poured into 100 mL 15% aqueous HCL solution. The betulonic acid (2.7 g) is obtained after the precipitate is filtered, washed with water, and dried.

Workup

  1. additionadded dropwise at 0° C
  2. customquench with methanol (100 mL)
  3. stirringstir for 5 minutes
  4. additionadd H2O (200 mL)
  5. customRemove organic solvent under vacuum, and then separate the precipitate
  6. filtrationby filtration
  7. washWash precipitate on the
  8. filtrationfilter with cooled water
  9. customdry
  10. customto obtain crude material
  11. filtrationThe solution is then filtered through a layer of aluminum oxide
  12. additionthe eluate is treated with an aqueous 10% KOH solution until complete precipitation
  13. customThe precipitate is then separated by filtration
  14. washwashed with 10 mL
  15. temperaturecooled benzene
  16. customdried
  17. customto obtain white solid
  18. additionthe solution is poured into 100 mL 15% aqueous HCL solution

Sources & evidence

ORD record
ord-b71e2df60dce4d68994a7c917928652b
Source dataset
uspto-grants-2012_01
Patent number
US08088757B2

Reaction notes

Loading…