Tetrahydrofuran → HCID 72714572, compound

HRID 1775764Notes

Reaction equation

HRID 1775764 reaction equation
[C:1](/[C:4](=[CH:23]\[C:24](\[CH3:39])=[CH:25]\[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[CH2:5][CH:6]([CH3:22])[C:7]([O:9][CH:10]1[C:14](=[O:15])[O:13][CH:12]([C:16]([OH:18])=[O:17])[CH:11]1[C:19]([OH:21])=[O:20])=[O:8])([OH:3])=[O:2].C1C[O:43]CC1.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1](/[C:4](=[CH:23]\[C:24](\[CH3:39])=[CH:25]\[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[CH2:5][CH:6]([CH3:22])[C:7]([O:9][CH:10]([C:14]([OH:43])=[O:15])[CH:11]([C:19]([OH:21])=[O:20])[CH:12]([OH:13])[C:16]([OH:18])=[O:17])=[O:8])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 72700712HCID 72700712, compound

Product 1

HCID 72714572HCID 72714572, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 1) To Compound 1 (1.33 g, 2.41 mmol), THF (20 mL), water (20 mL), and sodium carbonate (1.02 g, 9.62 mmol) were added, and the resulting mixture was stirred at room temperature for 30 minutes. The solvent in the reaction mixture was evaporated under reduced pressure. The resulting residue was purified by Diaion (registered trademark) HP-20ss (Mitsubishi Chemical Corporation) column chromatography (water/methanol), and to the residue, water (20 mL) and Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) (10 g) were added, and the resulting mixture was gently stirred at room temperature for 30 minutes. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by high performance liquid chromatography (column: Waters SunFire (registered trademark) C18, 19×250 mm, Cat. No. 186002669; mobile phase: acetonitrile containing 0.1% TFA/water containing 0.1% TFA), whereby 1-{(4Z,6E)-4-carboxy-2,6,8,10,12,14-hexamethylhexadec-4,6-dienoyloxy}-3-hydroxypropane-1,2,3-tricarboxylic acid (174 mg) was obtained.

Workup

  1. customThe solvent in the reaction mixture was evaporated under reduced pressure
  2. customThe resulting residue was purified by Diaion (registered trademark) HP-20ss (Mitsubishi Chemical Corporation) column chromatography (water/methanol)
  3. additionto the residue, water (20 mL) and Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) (10 g) were added
  4. stirringthe resulting mixture was gently stirred at room temperature for 30 minutes
  5. filtrationThe reaction mixture was filtered
  6. extractionthe filtrate was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting residue was purified by high performance liquid chromatography (column

Sources & evidence

ORD record
ord-3537d52079ff4725b4797b10f781392a
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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