反应详情

4-{[(tert-Butoxycarbonyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylic acid (729 mg, 2.81 mmol) was dissolved in N,N-dimethylformamide (7.3 mL) and cooled with an ice bath. To the solution was added sodium hydride, 60% in mineral oil (337 mg, 8.43 mmol), and the solution was warmed to room temperature. Dimethyl sulfate (612 μL, 6.47 mmol) was added, and the mixture was heated at 50° C. After 30 minutes, the reaction was cooled to room temperature, and additional 60% sodium hydride in mineral oil (56.2 mg, 1.40 mmol) and dimethyl sulfate (133 μL, 1.40 mmol) were added: The mixture was then heated at 50° C. for 1 hour. The reaction was cooled with an ice bath and quenched into a cold (ice bath temperature) mixture of 1 N hydrogen chloride (19.7 mL) and saturated sodium chloride (19.7 mL). The product was extracted with ethyl acetate (3 times). The organic solution was dried over anhydrous sodium sulfate and filtered. Concentration of the organic solution gave the title compound, which was used crude in the next step.

1. temperaturecooled with an ice bath
2. temperaturethe mixture was heated at 50° C
3. temperaturethe reaction was cooled to room temperature
4. temperatureThe mixture was then heated at 50° C. for 1 hour
5. temperatureThe reaction was cooled with an ice bath
6. customquenched into a cold (ice bath temperature) mixture of 1 N hydrogen chloride (19.7 mL) and saturated sodium chloride (19.7 mL)
7. extractionThe product was extracted with ethyl acetate (3 times)
8. dry with materialThe organic solution was dried over anhydrous sodium sulfate
9. filtrationfiltered