Реакция #1379896

Уравнение реакции

Water

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

N,N-diisopropylethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyloxy)acrylamide

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

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

Методика

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).

Источник