反应详情

Oxalyl chloride (0.19 g, 0.0015 moles) was added by syringe to a cold (10° C.) solution of trans-[[2-[[3,5-bis(1,1-dimethylethyl)phenyl]thio]cyclohexyl]thio]acetic acid (Example 5) (0.55 g, 0.0014 moles) in benzene (50 ml). The cold bath was removed, and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated to an oil using a rotary evaporator. The oil was dissolved in toluene (50 ml) and concentrated to an oil. The process was repeated using tetrahydrofuran (25 ml) instead of toluene. The residue was dissolved in tetrahydrofuran (50 ml). To this solution was added 2-(2-methylaminoethyl)pyridine (0.19 g, 0.0014 moles) and triethylamine (0.22 g), and the reaction mixture was stirred at room temperature for 48 hours. The white solid precipitate was removed by filtration and washed with ethyl acetate (25 ml). The filtrate was concentrated to give the crude product as an oil. The product was purified by silica gel chromatography and dried in vacuo at 100° C. for 1 hour to give the title compound. The structure assignment was supported by NMR, infrared spectroscopy and elemental analysis.

1. customThe cold bath was removed
2. concentrationThe reaction mixture was concentrated to an oil
3. customa rotary evaporator
4. dissolutionThe oil was dissolved in toluene (50 ml)
5. concentrationconcentrated to an oil
6. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
7. stirringthe reaction mixture was stirred at room temperature for 48 hours
8. customThe white solid precipitate was removed by filtration
9. washwashed with ethyl acetate (25 ml)
10. concentrationThe filtrate was concentrated
11. customto give the crude product as an oil
12. customThe product was purified by silica gel chromatography
13. customdried in vacuo at 100° C. for 1 hour