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

HRID 1646300Notes

Reaction equation

HRID 1646300 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f470bdd40f6643dc8815adedaa7592b8
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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