反应详情

Pyridine (0.83 mL, 10.3 mmol) and 1,2-dihydro-1-(1-naphthalenyl)-5H-tetrazole-5-thione (2.14 g, 9.38 mmol) were added to a solution of methyl 2-bromoacetate (977 μL, 10.3 mmol) in DMSO (50 mL). The resulting light yellow solution was stirred at room temperature for 2 h. The reaction mixture was then diluted with EtOAc (300 ml) and was successively washed with water (2×250 ml) and brine (100 ml), dried (MgSO4), filtered and concentrated under reduced pressure. The crude ester was dissolved in THF and aqueous 1 N NaOH solution was added. The solution was stirred at room temperature for 30 min. The THF was evaporated under reduced pressure and the residue was dissolved in aqueous 1 N NaOH solution. The solution was slowly acidified to pH 2 at 0° C. with aqueous 1 N HCl solution. The suspension was filtered and the resulting solid was rinsed with water and dried under reduced pressure to give the title compound (2.48 g, 92% yield) as a white solid.

1. washwas successively washed with water (2×250 ml) and brine (100 ml)
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. dissolutionThe crude ester was dissolved in THF
6. additionaqueous 1 N NaOH solution was added
7. stirringThe solution was stirred at room temperature for 30 min
8. customThe THF was evaporated under reduced pressure
9. dissolutionthe residue was dissolved in aqueous 1 N NaOH solution
10. customwas slowly acidified to pH 2 at 0° C. with aqueous 1 N HCl solution
11. filtrationThe suspension was filtered
12. washthe resulting solid was rinsed with water
13. customdried under reduced pressure