Réaction #1379896

Équation de réaction

Water

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

N,N-diisopropylethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyloxy)acrylamide

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autrethe layers were separated
3. 3
   LavageThe organic solution was washed with diluted hydrochloric acid
4. 4
   SéchageThe organic layer was dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent removed under reduced pressure
7. 7
   AutreThe residue was purified by flash chromatography
8. 8
   workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
9. 9
   AutreThe purification

Mode opératoire

A solution of acryloyl chloride dissolved in dry dichloromethane was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) and N,N-diisopropylethylamine in dry dichloromethane was added. Water was added after 16 hours of reaction and the layers were separated. The organic solution was washed with diluted hydrochloric acid, a saturated sodium bicarbonate solution, water, and brine. The organic layer was 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). The purification gave N-(tert-butoxycarbonyl), N-(tert-butoxycarbonyloxy)acrylamide (32).

Source