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

HRID 1443662ノート

反応式

HRID 1443662 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
  6. dry with materialethyl acetate (200 mL) and dry 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-a9c7858ecb014f65a5fe5c45f23c9e0c
出典データセット
uspto-grants-2010_02
特許番号
US07662771B2

反応ノート

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