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

HRID 1254930Notes

Reaction equation

HRID 1254930 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].C1CCN2C(=NCCC2)CC1.[CH:19]1([N:25]=[C:26]=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.Cl>[OH-].[Na+]>[CH:19]1([NH:25][C:26](=[O:27])[NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 18502Cyclohexyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 64201194-[(Cyclohexylcarbamoyl)amino]butanoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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

Workup

  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

Sources & evidence

ORD record
ord-42126cac1b3744d0b46120b313a1480b
Source dataset
uspto-grants-2013_06
Patent number
US08455652B2

Reaction notes

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