Hydrochloric Acid → methyl 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]hexanoate

HRID 1757195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757195
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:7]([CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Cl.[H][H].[CH3:29]O>[Pt]=O>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:29])=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 540265716-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]-4-hexenoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10045104methyl 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 82844Platinum oxide (PtO)Katalysator

Versuchsvorschrift

6-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]-4-hexenoic acid was converted to the methyl ester with methanol and ethereal hydrochloric acid. This methyl ester (302 mg) in methanol was hydrogenated with platinum oxide (25 mg) at one atmosphere of hydrogen for 2 hours. The isolated crude reduced ester was chromatographed over silica gel with 3:1 ethyl acetate/hexane to provide 0.125 g of methyl 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]hexanoate. Basic hydrolysis of this ester with potassium hydroxide as described in Example 11(ii) provided 6-[2-n- butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-hexanoic acid hydrochloride; mp 144°-145° C. (from acetone).

Aufarbeitung

  1. customThe isolated crude reduced ester
  2. customwas chromatographed over silica gel with 3:1 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-572956764cb54cbb87d5da880ac04f1c
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05444080

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