3-Acetamidophthalic Anhydride → alpha-Hexyl-4-{[3-(acetylamino)-2-carboxybenzoyl]-amino}-1H-imidazole-1-acetic acid ethyl ester

HRID 864682

Reaktionsgleichung

Reaktionsgleichung von HRID 864682
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:6]1[CH:10]=[C:9]([N+:11]([O-])=O)[N:8]=[CH:7]1)[CH3:2].[C:21]([NH:24][C:25]1[CH:35]=[CH:34][CH:33]=[C:27]2[C:28]([O:30][C:31](=[O:32])[C:26]=12)=[O:29])(=[O:23])[CH3:22]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:6]1[CH:10]=[C:9]([NH:11][C:28](=[O:29])[C:27]2[CH:33]=[CH:34][CH:35]=[C:25]([NH:24][C:21](=[O:23])[CH3:22])[C:26]=2[C:31]([OH:32])=[O:30])[N:8]=[CH:7]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 2261213-Acetamidophthalic AnhydrideHCID 10062368Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate

Produkt 1

HCID 54002110alpha-Hexyl-4-{[3-(acetylamino)-2-carboxybenzoyl]-amino}-1H-imidazole-1-acetic acid ethyl esterAusbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following the procedure of Example 2, 1.54 g of 4-nitro-α-hexyl-1H-imidazole-1-acetic acid ethyl ester were hydrogenated to the corresponding amine and allowed to react with 1.12 g of 3-acetamidophthalic anhydride in ethyl acetate. After stirring at room temperature, the solution was concentrated in vacuo and a small amount ethyl acetate added. After sitting overnight, the resulting solid was collected by filtration. Crystallization from hot ethyl acetate/methanol/ hexanes provided 0.54 g of the desired intermediate, m.p. 144'-145° C. NMR.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. additiona small amount ethyl acetate added
  3. filtrationthe resulting solid was collected by filtration
  4. customCrystallization from hot ethyl acetate/methanol/ hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bd31e7c3ee5347f9bb3c6391c432df1a
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563278

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