Acetate → HCID 44559683, compound

HRID 430905Notes

Reaction equation

HRID 430905 reaction equation
[CH3:1][C:2](OC(C)=O)=[O:3].CCCCCC.CCOC(C)=O.[CH3:20][CH:21]([C:23]([C@@:25]12[C@@:35]([CH2:37][CH2:38][CH:39]=[C:40]([CH3:42])[CH3:41])([CH3:36])[C@@H:34]([CH2:43][CH:44]=[C:45]([CH3:47])[CH3:46])[CH2:33][C@@:30]([CH2:48][CH:49]=[C:50]([CH3:52])[CH3:51])([C:31]1=[O:32])[C:29]([OH:53])=[C:28]([CH2:54][CH:55]=[C:56]([CH3:58])[CH3:57])[C:26]2=[O:27])=[O:24])[CH3:22].C([O-])(=O)C>O>[CH3:22][CH:21]([C:23]([C@:25]12[C@@:35]([CH2:37][CH2:38][CH:39]=[C:40]([CH3:41])[CH3:42])([CH3:36])[C@@H:34]([CH2:43][CH:44]=[C:45]([CH3:46])[CH3:47])[CH2:33][C@@:30]([CH2:48][CH:49]=[C:50]([CH3:52])[CH3:51])([C:31]1=[O:32])[C:29]([O:53][C:2]([CH3:1])=[O:3])=[C:28]([CH2:54][CH:55]=[C:56]([CH3:58])[CH3:57])[C:26]2=[O:27])=[O:24])[CH3:20]

Participants

6

Reactant 4

HCID 175AcetateHCID 7918Acetic AnhydrideHCID 441298CHEBI:5834HCID 21226206Ethyl acetate hexane

Product 1

HCID 44559683HCID 44559683, compoundYield 0.28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12 g of the plant extract obtained in Example 1 in 48 mL of pyridine was added to 9.8 mL of Ac2O and stirred at room temperature. The reaction was monitored by thin layer chromatography (TLC) (hexane-EtOAc 95:5; hyperforin Rf: 0.24; acetate Rf: 0.49). After 24 hours, the reaction mixture was diluted with water and extracted with a 3:1 hexane-ether mixture. The organic phase was washed with dilute HCl, saturated NaHCO3, and saline solution. After drying (Na2SO4) and evaporation, the residue was purified by chromatography on a silica gel column (ca 30 g), eluted first with petroleum ether to remove fats, then using hexane-EtOAc 95:5 as soon as the title compound started to elute. Hyperforin acetate (3.34 g, 0.28%) was obtained as a colorless paste with the following properties:

Workup

  1. extractionA solution of 12 g of the plant extract
  2. customobtained in Example 1 in 48 mL of pyridine
  3. extractionextracted with a 3:1 hexane-ether mixture
  4. washThe organic phase was washed with dilute HCl, saturated NaHCO3, and saline solution
  5. customAfter drying
  6. custom(Na2SO4) and evaporation
  7. customthe residue was purified by chromatography on a silica gel column (ca 30 g)
  8. washeluted first with petroleum ether
  9. customto remove fats
  10. washto elute

Sources & evidence

ORD record
ord-1332a2ccd4f14ab59c36cb213905bd8f
Source dataset
uspto-grants-2003_12
Patent number
US06656510B2

Reaction notes

Loading…