Reacción #1379896

Ecuación de reacción

Water

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

N,N-diisopropylethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyloxy)acrylamide

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente