Hydrochloric Acid → 3-[(2-Mercaptomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid

HRID 1646298Notes

Reaction equation

HRID 1646298 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:16]=[C:17]([CH2:19][CH3:20])[CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=O)C.N1CCCC1.Cl>O>[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:16]=[C:17]([CH2:19][CH3:20])[CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 156702113-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid

Product 1

HCID 156702123-[(2-Mercaptomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acidYield 33.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid (compound of Example 64) (1.0 g) is suspended in water (10 ml), and thereto is added pyrrolidine (0.6 g) under nitrogen, and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is adjusted to pH 1 with conc. hydrochloric acid and is extracted with ethyl acetate (100 ml). The extract is washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure. The residue is dissolved in methanol and purified by a medium pressure column chromatography with CHP-20P (eluant, water-methanol). The fractions containing the desired compound are collected and concentrated into dryness to give the title compound (0.3 g).

Workup

  1. extractionis extracted with ethyl acetate (100 ml)
  2. washThe extract is washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate, and ethyl acetate
  4. distillationis distilled off under reduced pressure
  5. dissolutionThe residue is dissolved in methanol
  6. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-methanol)
  7. additionThe fractions containing the desired compound
  8. customare collected
  9. concentrationconcentrated into dryness

Sources & evidence

ORD record
ord-2c28fb25d7514caeaca7f383024e85a0
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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