Sodium Chloride → HCID 23139002, compound

Participants

Reaction Steps

To a solution of (E)-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (13.22 g) in toluene (200 ml) were added thioacetic acid (3.7 ml) and N,N-dimethylformamide dineopentyl acetal (14.5 ml) with stirring at room temperature, and the resulting mixture was stirred at the same temperature for 2 hours. After addition of aqueous sodium chloride solution, products were extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and the organic layer was dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography using a mixed solvent of ethyl acetate and hexane (2:1) as the eluent to afford 5-((acetylsulfanyl){1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (8.17 mg, yield: 55%) as a pale yellow amorphous solid.

Provenance & Evidence