Triethylamine → 3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid

HRID 1646278Notes

Reaction equation

HRID 1646278 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:25](Cl)=[O:26])(=[O:21])[CH3:20]>O1CCCC1>[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:25]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6])=[O:26])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chlorideHCID 184056783-Amino-5-methylbenzoic acid

Product 1

HCID 156701493-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acidYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Amino-5-methylbenzoic acid (1.9 g) is dissolved in a 60% aqueous solution of tetrahydrofuran (30 ml) containing triethylamine (2.3 g), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenylpropionyl chloride (3.2 g) in tetrahydrofuran (20 ml) with stirring under ice cooling, and the mixture is stirred at room temperature for 2 hours. Tetrahydrofuran is distilled off under reduced pressure, and the residue is extracted with ethyl acetate (100 ml). The extract is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate is distilled off under reduced pressure. The residue is dissolved in acetonitrile and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desited compound are collected and concentrated into dryness under reduced pressure to give the title compound (2.4 g).

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. distillationTetrahydrofuran is distilled off under reduced pressure
  3. extractionthe residue is extracted with ethyl acetate (100 ml)
  4. washThe extract is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationethyl acetate is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in acetonitrile
  8. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  9. additionThe fractions containing the desited compound
  10. customare collected
  11. concentrationconcentrated into dryness under reduced pressure

Sources & evidence

ORD record
ord-9521ba2fe65f4fb7b46b26001677f5a2
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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