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

HRID 1254930

Reaktionsgleichung

Reaktionsgleichung von HRID 1254930
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-42126cac1b3744d0b46120b313a1480b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455652B2

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