Water → HCID 15284532, compound

HRID 273833Notes

Reaction equation

HRID 273833 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[C:7]([CH2:10][C:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(C(OCC)=O)[C:12]([O:14]CC)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+].O>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[C:7]([CH2:10][CH:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57435951HCID 57435951, compound

Product 1

HCID 15284532HCID 15284532, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]methyl-2-benzylmalonate (0.72 g, 1.36 mmol), potassium hydroxide (0.83 g, 14.7 mmol), water (15 mL) and ethanol (25 mL) was refluxed for 4 hours. The ethanol was evaporated, the residual aqueous layer was extracted with diethyl ether, and the basic solution was adjusted to pH 3.75 with concentrated hydrochloric acid. The precipitated product was extracted into methylene chloride, dried, and concentrated. This crude product was flash chromatographed on silica gel with 10% methanol in methylene chloride to give 0.51 g (86%) of 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzylpropanoic acid; mp 118°-120° C. (from acetone/diethyl ether as the hydrochloride salt).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe ethanol was evaporated
  3. extractionthe residual aqueous layer was extracted with diethyl ether
  4. extractionThe precipitated product was extracted into methylene chloride
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-813f42682d674ab19848b870f46d9e9b
Source dataset
uspto-grants-1995_02
Patent number
US05387601

Reaction notes

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