Hydrochloric Acid → HCID 15670199, compound

HRID 248683Notes

Reaction equation

HRID 248683 reaction equation
C([S:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=O)C.[OH-].[Na+].Cl>CO>[SH:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]([CH3:28])[CH3:27])=[CH:24][CH:25]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15670193HCID 15670193, compound

Product 1

HCID 15670199HCID 15670199, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-[[2-Acetylthiomethyl-3-(4-dimethylaminophenyl)-propionyl]amino]benzoic acid (compound of Example 45) (2.6 g) is dissolved in 50% aqueous methanol (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 4.5 with 10% hydrochloric acid, and methanol is distilled off. The resulting aqueous solution 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 and the residue is lyophilized to give the title compound (0.7 g).

Workup

  1. distillationis distilled off
  2. customThe resulting aqueous solution is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  3. additionThe fractions containing the desired compound
  4. customare collected
  5. distillationacetonitrile is distilled off

Sources & evidence

ORD record
ord-02a0677e449143de9b6f11fcccedfcf9
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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