Hydrochloric Acid → HCID 15670192, compound

HRID 1646290Notes

Reaction equation

HRID 1646290 reaction equation
[Na+].C([S:5][CH2:6][CH:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[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]([F:27])=[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 23701009HCID 23701009, compound

Product 1

HCID 15670192HCID 15670192, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[[2-Acetylthiomethyl-3-(4-fluorophenyl)propionyl]amino]benzoic acid sodium salt (compound- of Example 40) (1.2 g) is dissolved in water (20 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-dioxane). The fractions containing the desired compound are collected and 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-dioxane)
  5. additionThe fractions containing the desired compound
  6. customare collected

Sources & evidence

ORD record
ord-735a818164874fc797b0818f4880b5ca
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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