Hydrochloric Acid → Mangostin

HRID 1257135Notes

Reaction equation

HRID 1257135 reaction equation
CC(C)=CCC1C(O)=CC2OC3C=C(O)C(O)=C(CC=C(C)C)C=3C(=O)C=2C=1O.[CH3:30][C:31]([CH3:60])=[CH:32][CH2:33][C:34]1[C:39]([OH:40])=[C:38]2[C:41]([C:43]3[C:48]([CH2:49][CH:50]=[C:51]([CH3:53])[CH3:52])=[C:47]([O:54][CH3:55])[C:46]([OH:56])=[CH:45][C:44]=3[O:57][C:37]2=[CH:36][C:35]=1[O:58]C)=[O:42].[C-]#N.[Na+].Cl>CS(C)=O>[CH3:30][C:31]([CH3:60])=[CH:32][CH2:33][C:34]1[C:39]([OH:40])=[C:38]2[C:41]([C:43]3[C:44]([O:57][C:37]2=[CH:36][C:35]=1[OH:58])=[CH:45][C:46]([OH:56])=[C:47]([O:54][CH3:55])[C:48]=3[CH2:49][CH:50]=[C:51]([CH3:53])[CH3:52])=[O:42]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 5464078gamma-MangostinHCID 5495925beta-Mangostin2×

Product 1

HCID 5281650MangostinYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
195 °C

Procedure

γ-Mangostin from β-mangostin: To a solution of β-mangostin (0.25 g, 0.58 mmol) in DMSO (LR, 15 mL) was added sodium cyanide (0.52 g, 10.61 mmol) at RT and the mixture was stirred at 190-200° C. for 6 h. The reaction mixture was allowed to cool to ambient temperature and then poured into ice water and the mixture was acidified with dil. HCl. The solution was extracted with ethyl acetate (5×50 mL). The combined ethyl acetate layer was washed with aqueous potassium permanganate (10%), water, brine and dried over sodium sulfate. The solution was filtered and treated with few drops of triethyl amine and the solvent evaporated. The residue was chromatographed over silica gel column using hexane/ethyl acetate mixture (80:20) as an eluent to give α-mangostin (90 mg, 37%). The α-mangostin was then converted to γ-mangostin using the inventive demethylation procedure as described in example 12.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe solution was extracted with ethyl acetate (5×50 mL)
  3. washThe combined ethyl acetate layer was washed with aqueous potassium permanganate (10%), water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. additiontreated with few drops of triethyl amine
  7. customthe solvent evaporated
  8. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-e29949fa0222415c96995968cd95f3fe
Source dataset
uspto-grants-2013_06
Patent number
US08461360B2

Reaction notes

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