Gamma-Aminobutyric Acid → 4-[(Cyclohexylcarbamoyl)amino]butanoic acid

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.

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

ORDレコード

ord-04cc692e0d2d4711baa0616f6cee78a8

出典データセット

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08476043B2