Toluene → (E)-3-2-n-Butyl-1-{(4-carboxy-2-chlorophenyl)methyl}-1H-imidazol-5-yl-2-benzyl-2-propenoic Acid

HRID 1033903Notes

Reaction equation

HRID 1033903 reaction equation
C([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][C:14]=2[Cl:24])[C:7]([CH:10]=O)=[CH:8][N:9]=1)CCC.N1[CH2:30][CH2:29][CH2:28][CH2:27]C1.[C:31]1([CH3:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH3:30][CH:29]([N:9]1[CH:8]=[C:7](/[CH:10]=[C:16](\[CH2:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)/[C:19]([OH:21])=[O:20])[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=2[Cl:24])[CH2:5]1)[CH2:28][CH3:27]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 8082PiperidineHCID 199367892-n-Butyl-1-(4-carboethoxy-2-chlorobenzyl)imidazole-5-aldehyde

Product 1

HCID 86747876(E)-3-2-n-Butyl-1-{(4-carboxy-2-chlorophenyl)methyl}-1H-imidazol-5-yl-2-benzyl-2-propenoic Acid

Procedure

A solution of this half-acid half-ester in toluene is added to a refluxing solution of 2-n-butyl-1-(4-carboethoxy-2-chlorobenzyl)imidazole-5-aldehyde and piperidine in toluene. Twice at 1 hour intervals an additional amounts of the half-acid, half-ester is added, and the solution is then refluxed for 17 hours. Evaporation of the toluene and chromatography of the residue over silica gel using 2:3 ethyl acetate-hexane for elution gives the diester of the title product. This diester is hydrolyzed in 2:1 ethanol-water with 5 equivalents of potassium hydroxide for 18 hours and worked up in the usual manner to give the final product.

Workup

  1. temperaturethe solution is then refluxed for 17 hours
  2. customEvaporation of the toluene and chromatography of the residue over silica gel using 2:3 ethyl acetate-hexane
  3. washfor elution

Sources & evidence

ORD record
ord-563c53c70eb04809a1c6009e861f5657
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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