Réaction #531854

Équation de réaction

HCl

4-aminobutyric acid

DBU

cyclohexyl isocyanate

→

4-(3-Cyclohexyl-ureido)-butyric acid

Rendement 76.0%

Solvants

NaOH

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe mixture was strongly mixed at room temperature overnight
2. 2
   FiltrationThe formed white solid was collected by filtration
3. 3
   AutreThe mixture was purified by chromatography on a silica column (8×3 cm)
4. 4
   LavageElution with a mixture 50:50:1 of hexane
5. 5
   Autreethyl acetate:acetic acid gave the pure targeted product

Mode opératoire

To a cold solution of 4-aminobutyric acid (2.16 g, 21 mmol) and catalytic amount of DBU in 22 mL of 1.0 N NaOH, 2.5 g (20 mmol) of cyclohexyl isocyanate were added in one time. The mixture was strongly mixed at room temperature overnight. The reaction was then acidified with concentrated HCl. The formed white solid was collected by filtration. The mixture was purified by chromatography on a silica column (8×3 cm). Elution with a mixture 50:50:1 of hexane:ethyl acetate:acetic acid gave the pure targeted product. The resulting white crystal (3.46 g; yield: 76%) had a mp of 153.0-154.0° C. [M+H]+ 281.18.

Source