Reaction #1379896

Reaction equation

Water

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

N,N-diisopropylethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyloxy)acrylamide

Solvents

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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