Реакция #46659

Уравнение реакции

N-Methylmorpholine

isobutyl chloroformate

ammonia

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

→

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

Выход 58.0%

Растворители

tetrahydrofuran

Chloroform

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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.

Источник