반응 #1379899

반응 방정식

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

triethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyl),N-(tert-butoxycarbonyloxy)acrylamide

수율 28.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas slowly added over a period of 1 hour to the cooled solution
2. 2
   기타The ice bath was removed after 4 hours
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   온도warmed up gradually to room temperature
5. 5
   workup.ADDITIONWater (100 mL) was added to the reaction
6. 6
   기타the layers were separated
7. 7
   세척The organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL)
8. 8
   건조The organic layer was then dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    기타the solvent removed under reduced pressure
11. 11
    기타The residue was purified by flash chromatography
12. 12
    workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
13. 13
    세척to elute the product
14. 14
    기타The purification

실험 절차

A solution of acryloyl chloride (700 μL; 779.8 mg; 8.6 mmole) dissolved in dry dichloromethane (20 mL) was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) (2.0038 g; 8.6 mmole) and triethylamine (1.32 mL; 958.3 mg; 9.5 mmole) in dry dichloromethane (20 mL) was slowly added over a period of 1 hour to the cooled solution. The ice bath was removed after 4 hours and the reaction mixture was left stirring overnight while its temperature warmed up gradually to room temperature. Water (100 mL) was added to the reaction and the layers were separated. The organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL). The organic layer was then dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate (90:10) to elute the product. The purification gave 690 mg (28%) of N-(tert-butoxycarbonyl),N-(tert-butoxycarbonyloxy)acrylamide (32) as a colorless oil.

출처