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

HRID 260752Notes

Reaction equation

HRID 260752 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

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).

Workup

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

Sources & evidence

ORD record
ord-ec4fcfbcb25c412ea8d4a27c6005e465
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

Loading…