Hydrochloric Acid → Hydroxy Tipelukast

Participants

Reaction Steps

A mixed solution of 42.6 mg of (+)-4-[3-(3-chloropropoxy)-6-(1-hydroxyethyl)-2-propylphenoxy] butanoic acid, 30.0 mg of (2-hydroxy-4-mercapto-3-propylphenyl) ethanone, 39.4 mg of potassium carbonate and 1 ml of dimethylformamide was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. After washed with water and saturated aqueous solution of sodium chloride, the organic layer was dried over anhydrous sodium sulfate and subjected to distillation off of the solvent under reduced pressure to afford residue. The residue was purified through silica gel column chromatography (methylene chloride: ethanol=20:1) and further through preparative thin layer chromatography (methylene chloride: methanol=1.5:1) to afford 16.1 mg of yellow oily water as the title compound (yield 25.4%). [α]D20 +13.3° (c=1.56, ethanol)

Provenance & Evidence