(+)-Ursolic Acid → Sodium oleanolate

HRID 1943580Notes

Reaction equation

HRID 1943580 reaction equation
[CH3:1][C@H:2]1[C@H:28](C)[C@@H:27]2[C@@:5]([C:31]([OH:33])=[O:32])([CH2:6][CH2:7][C@@:8]3([CH3:30])[C@:13]4([CH3:26])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[CH2:19][CH2:18][C@:17]5([CH3:25])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.[CH3:34][O-].[Na+:36]>CO.C(Cl)(Cl)Cl>[CH3:25][C@@:17]12[C@H:12]3[CH2:11][CH:10]=[C:9]4[C@@H:27]5[CH2:28][C:2]([CH3:34])([CH3:1])[CH2:3][CH2:4][C@:5]5([C:31]([O-:33])=[O:32])[CH2:6][CH2:7][C@@:8]4([CH3:30])[C@:13]3([CH3:26])[CH2:14][CH2:15][C@H:16]1[C:21]([CH3:22])([CH3:23])[C@@H:20]([OH:24])[CH2:19][CH2:18]2.[Na+:36]

Participants

4

Reactant 2

HCID 64945(+)-Ursolic AcidHCID 10942334Sodium Methoxide

Product 1

HCID 49857633Sodium oleanolate

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

30 mg of 3-O-(α-L-arabopyranosyl) ursolic acid was dissolved in methanol/chloroform (4 ml, 3/1), added with 5 mg of NaOMe, then stirred at room tempreature for 30 min and filtered to separate out a white solid. The solid was washed with methanol and dried to obtain 3-O-(α-L-arabopyranosyl) ursolic acid sodium salt.

Workup

  1. filtrationfiltered
  2. customto separate out a white solid
  3. washThe solid was washed with methanol
  4. customdried

Sources & evidence

ORD record
ord-78ac1975e6e742679e5d252709b186c0
Source dataset
uspto-grants-2013_03
Patent number
US08394776B2

Reaction notes

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