Reacción #11533

Ecuación de reacción

N-Methylmorpholine

isobutyl chloroformate

ammonia

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

→

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

Rendimiento 58.0%

Disolventes

tetrahydrofuran

Chloroform

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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 then a solution of isobutyl chloroformate (0.38 ml, 2.9 mmol) in tetrahydrofuran (3 ml) were added to the mixture. After one hour, a 28% aqueous ammonia solution (6.0 ml, 9.8 mmol) was added thereto, and the whole was stirred for 1.5 hours. Chloroform (50 ml) was added to the reaction mixture, 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 residue was purified by silica gel column chromatography to give 0.34 g (58%) of 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionamide as colorless crystals.

Fuente