Water → HCID 15284532, compound

HRID 377232Notes

Reaction equation

HRID 377232 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-chloro-phenyl)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-8680751c45fe4d51bffd0c35ef9e6c21
Source dataset
uspto-grants-2000_02
Patent number
US06025380

Reaction notes

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