Hydrochloric Acid → HCID 15670191, compound

HRID 1646289Notes

Reaction equation

HRID 1646289 reaction equation
[Na+].C([S:5][CH2:6][CH:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([O-:16])=[O:15])=[O:9])(=O)C.[OH-].[Na+].Cl>O>[SH:5][CH2:6][CH:7]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23701007HCID 23701007, compound

Product 1

HCID 15670191HCID 15670191, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[[2-Acetylthiomethyl-3-(4-methoxyphenyl)propionyl]amino]benzoic acid sodium salt (compound of Example 36) (1.8 g) is dissolved in water (30 ml), and the mixture is adjusted to pH 12.0 with 10% aqueous sodium hydroxide solution under nitrogen. After reacting at room temperature for one hour, the reaction mixture is adjusted to pH 2.5 with 10% hydrochloric acid. The mixture is extracted with ethyl acetate (50 ml). The extract is washed with water and ethyl acetate is distilled off. 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 acetonitrile is distilled off under reduced pressure and the residue is lyophilized to give the title compound (0.6 g).

Workup

  1. extractionThe mixture is extracted with ethyl acetate (50 ml)
  2. washThe extract is washed with water and ethyl acetate
  3. distillationis distilled off
  4. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  5. additionThe fractions containing the desired compound
  6. customare collected
  7. distillationacetonitrile is distilled off under reduced pressure

Sources & evidence

ORD record
ord-91eb0ad542264f7295463f145763c2ee
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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