Réaction #1379899

Équation de réaction

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

triethylamine

acryloyl chloride

→

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

Rendement 28.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas slowly added over a period of 1 hour to the cooled solution
2. 2
   AutreThe ice bath was removed after 4 hours
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Températurewarmed up gradually to room temperature
5. 5
   workup.ADDITIONWater (100 mL) was added to the reaction
6. 6
   Autrethe layers were separated
7. 7
   LavageThe 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
   SéchageThe organic layer was then dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Autrethe solvent removed under reduced pressure
11. 11
    AutreThe residue was purified by flash chromatography
12. 12
    workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
13. 13
    Lavageto elute the product
14. 14
    AutreThe purification

Mode opératoire

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.

Source