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

HRID 1444638

반응식

HRID 1444638 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5ccf381bfb94412b1c477a5d13b5954
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662910B2

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