(+)-Ursolic Acid → HCID 49773832, compound

HRID 2190249Notes

Reaction equation

HRID 2190249 reaction equation
[CH3:1][C@H:2]1[C@H:28]([CH3:29])[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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:29][CH:28]1[CH:27]2[C@@:5]([C:31]([OH:33])=[O:32])([CH2:6][CH2:7][C@:8]3([CH3:30])[C:9]2=[CH:10][CH2:11][CH:12]2[C@@:13]3([CH3:26])[CH2:14][CH2:15][CH:16]3[C@:17]2([CH3:25])[CH2:18][CH2:19][C:20](=[O:24])[C:21]3([CH3:22])[CH3:23])[CH2:4][CH2:3][CH:2]1[CH3:1]

Participants

4

Reactant 2

HCID 64945(+)-Ursolic AcidHCID 159087Triacetoxyperiodinane

Product 1

HCID 49773832HCID 49773832, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ursolic acid (2a, 1.0 g, 2.18 mmol) and CH2Cl2 (55 mL) was added the Dess-Martin reagent (1.2 g, 2.83 mmol) under nitrogen at room temperature. After stirring at room temperature for 2.5 hours, the starting material was consumed as indicated by TLC (1:1 hexanes:diethyl ether). The reaction mixture was quenched with the addition of a solution of sodium thiosulfate and NaHCO3 (6.3 g sodium thiosulfate in 25 mL saturated NaHCO3 solution). The mixture was stirred at room temperature for 10 minutes. The layers were separated and the aqueous layer was extracted with EtOAc (3×250 mL). The combined organics were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 3:1 hexanes/diethyl ether) to provide the sub-title compound (924 mg, 92%) as a white foam solid.

Workup

  1. customthe starting material was consumed
  2. customThe reaction mixture was quenched with the addition of a solution of sodium thiosulfate and NaHCO3 (6.3 g sodium thiosulfate in 25 mL saturated NaHCO3 solution)
  3. stirringThe mixture was stirred at room temperature for 10 minutes
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×250 mL)
  6. dry with materialThe combined organics were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica, 3:1 hexanes/diethyl ether)

Sources & evidence

ORD record
ord-da4fb458719b4c2d9c73f20331fbf16d
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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