Citric Acid → Benzoic acid, 3-[[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]amino]-

HRID 1646300ノート

反応式

HRID 1646300 の反応式
C([S:4][CH2:5][CH:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15]CC)=[O:14])=[O:8])(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[SH:4][CH2:5][CH:6]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([OH:15])=[O:14])=[O:8]

参加物

5

反応物 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 15670143Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

生成物 1

HCID 10286448Benzoic acid, 3-[[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]amino]-収率 76.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]benzoate (6.37 g) is dissolved in methanol (100 ml), and thereto is added 1N aqueous sodium hydroxide solution (49.5 ml) under ice cooling, and the mixture is stirred for hours under nitrogen. After stirring further at room temperature overnight, the reaction mixture is acidified with saturated aqueous citric acid solution, and methanol is distilled off under reduced pressure. To the residue is added water (50 ml), and the mixture is extracted with ethyl acetate. The extract is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated under reduced pressure, and the precipitates are separated by filtration to give the title compound (4 g).

後処理

  1. stirringAfter stirring further at room temperature overnight
  2. distillationis distilled off under reduced pressure
  3. additionTo the residue is added water (50 ml)
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  9. additionThe fractions containing the desired compound
  10. customare collected
  11. concentrationconcentrated under reduced pressure
  12. customthe precipitates are separated by filtration

出典と根拠

ORDレコード
ord-f470bdd40f6643dc8815adedaa7592b8
出典データセット
uspto-grants-1993_01
特許番号
US05179125

反応ノート

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