تفاعل #1379899

معادلة التفاعل

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

triethylamine

acryloyl chloride

→

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

المردود 28.0%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر