Citric Acid → HCID 15670228, compound

HRID 1646305Notes

Reaction equation

HRID 1646305 reaction equation
C([S:4][CH2:5][CH:6]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]([NH:9][C:10]([CH3:22])([CH3:21])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:8])(=O)C.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[SH:4][CH2:5][CH:6]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:7]([NH:9][C:10]([CH3:22])([CH3:21])[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:8]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 8471TriethylamineHCID 15670226HCID 15670226, compound

Product 1

HCID 15670228HCID 15670228, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Benzyl 2-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]isobutyrate (0.45 g) is dissolved in a mixture of methanol (5 ml) and water (3 ml) under nitrogen, and thereto is added triethylamine (0.22 g), and the mixture is stirred at room temperature for 5 hours. After the reaction, 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, and the mixture is extracted with chloroform. The extract is washed with water and dried over anhydrous magnesium sulfate, and then distilled under reduced pressure. The residue is purified by a silica gel column chromatography (eluant, chloroform) to give the title compound (0.35 g).

Workup

  1. customAfter the reaction
  2. distillationis distilled off under reduced pressure
  3. additionTo the residue is added water
  4. extractionthe mixture is extracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customThe residue is purified by a silica gel column chromatography (eluant, chloroform)

Sources & evidence

ORD record
ord-86e5c1ab19c14e6c86691497b39c9343
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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