Ammonium Acetate → 7-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid methyl ester

HRID 1039163Notes

Reaction equation

HRID 1039163 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][O:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=O)[NH:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])=O>C(O)(=O)C>[CH3:6][O:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[NH:5][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 684879257-[2-(2-Methoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester

Product 1

HCID 591677617-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Heat a mixture of ammonium acetate (16.5 g, 214 mmol) and 7-[2-(2-methoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester (14.2 g, 42.3 mmol) in acetic acid (300 mL) at reflux under nitrogen for 15 hours. Remove the solvent under reduced pressure. Dilute the residue in ethyl acetate (500 mL) and adjust to pH 8 with saturated aqueous sodium bicarbonate solution. Extract the aqueous layer with additional ethyl acetate (200 mL) and dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford 7-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid methyl ester (5.86 g, 44%): APCI mass spectrum m/z 317 [C18H24N2O3+H]+.

Workup

  1. temperatureHeat
  2. temperatureat reflux under nitrogen for 15 hours
  3. customRemove the solvent under reduced pressure
  4. additionDilute the residue in ethyl acetate (500 mL)
  5. extractionExtract the aqueous layer with additional ethyl acetate (200 mL)
  6. dry with materialdry the combined organic extracts over sodium sulfate
  7. customremove the solvent under reduced pressure
  8. customPurify the residue by flash column chromatography on silica gel
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0a58340062ce42dea444b2771bc9ba7e
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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