Reaktion #46659

Reaktionsgleichung

N-Methylmorpholine

isobutyl chloroformate

ammonia

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

→

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

Ausbeute 58.0%

Lösungsmittel

tetrahydrofuran

Chloroform

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle