HCID 23138651, compound → HCID 86609447, compound

Participants

Reaction Steps

The mixture (2.98 g) of (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol and (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol obtained in Example 166-(b) was dissolved in a mixed solvent of dichloromethane (40 ml) and toluene (40 ml), and thioacetic acid (1.3 ml) and N,N-dimethylformamide dineopentyl acetal (5.0 ml) were added thereto. After the mixture was stirred at room temperature for 2 hours, it was partitioned between water and ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure gave a residue, which was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:1:1) to afford (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (containing impurities, 1.52 g, gross yield: 46%) as the less polar isomer, and (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,4-triazol-3-yl]methylidene}-1-(triphenylmethyl)piperidine (2.08 g, yield: 62%) as the polar isomer, respectively.

Provenance & Evidence