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

HRID 1039163ノート

反応式

HRID 1039163 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-0a58340062ce42dea444b2771bc9ba7e
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

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