反応 #46659

反応方程式

N-Methylmorpholine

isobutyl chloroformate

ammonia

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

→

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

収率 58.0%

溶媒

tetrahydrofuran

Chloroform

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe whole was stirred for 1.5 hours
2. 2
   温度the temperature was raised to room temperature
3. 3
   洗浄the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (20 ml) successively
4. 4
   乾燥The organic layer was dried over magnesium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他the resulting residue was purified by silica gel column chromatography

実験手順

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.

出典