反应详情

温度

-10 °C

1-(1-(tert-Butoxycarbonyl)piperidin-4-yl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (355 mg, 1.140 mmol) was dissolved in a mixture of tetrahydrofuran (20 mL,) and N,N-dimethylformamide (15 μl, 0.194 mmol). Mixture was cooled to −10° C. Oxalyl chloride (150 μL, 1.714 mmol) was added to the mixture drop-wise. Reaction mixture was warmed to room temperature and held with stirring for 1 hour. Another 60 μL of oxalyl chloride was added to the mixture. Reaction stirred at room temperature for 30 minutes. Mixture was cooled to −10° C. Ammonia gas was bubbled through the mixture for 5 minutes. Reaction was held at −10° C. with stirring for 30 minutes. Mixture was warmed to room temperature and then diluted with water. Material was extracted three times with ethyl acetate and the aqueous phase was discarded. Material was washed with brine and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as off-white solid in 79% yield. MS (M−H)−=309.2.

1. customReaction mixture
2. temperaturewas warmed to room temperature
3. customReaction
4. stirringstirred at room temperature for 30 minutes
5. temperatureMixture was cooled to −10° C
6. customAmmonia gas was bubbled through the mixture for 5 minutes
7. customReaction
8. customwas held at −10° C.
9. stirringwith stirring for 30 minutes
10. temperatureMixture was warmed to room temperature
11. extractionMaterial was extracted three times with ethyl acetate
12. washMaterial was washed with brine
13. filtrationfiltered
14. concentrationconcentrated to dryness