Hydrochloric Acid → 4-[(2-Acetylthiomethyl-3-phenylpropionyl)aminomethyl]benzoic acid

HRID 248696Notes

Reaction equation

HRID 248696 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[C:17]([S:20][CH2:21][CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23](Cl)=[O:24])(=[O:19])[CH3:18].Cl>O.O1CCCC1>[C:17]([S:20][CH2:21][CH:22]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:23]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)=[O:24])(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 655264-(Aminomethyl)Benzoic AcidHCID 516892Sodium BicarbonateHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chloride

Product 1

HCID 156702224-[(2-Acetylthiomethyl-3-phenylpropionyl)aminomethyl]benzoic acidYield 32.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Aminomethylbenzoic acid (1.50 g) and sodium hydrogen carbonate (1.68 g) are suspended in water (20 ml), and thereto is added dropwise a solution of 2-acetylthiomethyl-3-phenylpropionyl chloride (2.86 g) in tetrahydrofuran (6 ml) with vigorously stirring. After the reaction is completed, the reaction mixture is acidified with hydrochloric acid and is extracted with ethyl acetate. The extract is dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is recrystallized from ethanol to give the title compound (1.2 g).

Workup

  1. extractionis extracted with ethyl acetate
  2. dry with materialThe extract is dried over anhydrous magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-e0e35feac4ad4b22ad21bedbc294e8a9
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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