Tetrahydrofuran → HCID 72714572, compound

Participants

Reaction Steps

(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.

Provenance & Evidence