Potassium Hydroxide → 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-hexanoic acid hydrochloride
Reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>>[ClH:26].[CH2:1]([C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
6-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-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-5-yl]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).
Sources & evidence
- ORD record
- ord-00f24509b4374099ba8c32104fd1bc6b
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05530017
Reaction notes
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