Reaction #531854

Reaction equation

HCl

4-aminobutyric acid

DBU

cyclohexyl isocyanate

→

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

Yield 76.0%

Solvents

NaOH

Conditions

Workup

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

Procedure

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