반응 #46659

반응 방정식

N-Methylmorpholine

isobutyl chloroformate

ammonia

3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionic acid

→

3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionamide

수율 58.0%

용매

tetrahydrofuran

Chloroform

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGthe whole was stirred for 1.5 hours
2. 2
   온도the temperature was raised to room temperature
3. 3
   세척the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (20 ml) successively
4. 4
   건조The organic layer was dried over magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타the resulting residue was purified by silica gel column chromatography

실험 절차

Next, anhydrous tetrahydrofuran (7 ml) was added to 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionic acid (0.59 g, 2.0 mmol), and the mixture was stirred at −78° C. N-Methylmorpholine (0.22 ml, 2.0 mmol) and a solution of isobutyl chloroformate (0.38 ml, 2.9 mmol) in tetrahydrofuran (3 ml) were added successively to the mixture. After one hour, a 28% aqueous ammonia solution (6.0 ml, 9.8 mmol) was added to the reaction mixture, and the whole was stirred for 1.5 hours. Chloroform (50 ml) was added thereto, the temperature was raised to room temperature, and the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (20 ml) successively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionamide (0.34 g, 58%) as colorless crystals.

출처