Bis-(1H-imidazol-2-YL)-methanone → (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester

HRID 1747375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747375
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@@H:6]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])[CH2:7][CH2:8][CH3:9])[CH3:2].[C:19](C1NC=CN=1)(C1NC=CN=1)=[O:20]>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@@H:6]([N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:19]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2]

Komponenten

4

Edukt 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 59497425(S)-3-(2-Amino-phenylamino)-hexanoic acid ethyl ester

Produkt 1

HCID 59497467(S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-(2-Amino-phenylamino)-hexanoic acid ethyl ester (650 mg, 2.6 mmol) in THF (10 mL) was added carbonyl diimidazole [CDI] (842 mg, 5.2 mmol) at room temperature under nitrogen atmosphere. The solution was stirred at the same temperature for 12 hours. The solution was concentrated and the residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (700 mg, 98%) as a colorless oil.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-a6b4107db982477e80ea2f34f50ee4cf
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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