Hydrochloric Acid → HCID 86746488, compound

HRID 1646293Notes

Reaction equation

HRID 1646293 reaction equation
[ClH:1].C([S:5][CH2:6][CH:7]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)[C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:14]([OH:16])=[O:15])=[O:9])(=O)C.[OH-].[Na+].Cl>CO>[ClH:1].[SH:5][CH2:6][CH:7]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)[C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:14]([OH:16])=[O:15])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86746489HCID 86746489, compound

Product 1

HCID 86746488HCID 86746488, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-[[2-Acetylthiomethyl-3-(4-dimethylaminophenyl)-propionyl]amino]5-methylbenzoic acid hydrochloride (compound of Example 59) (1.9 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 under reduced pressure. 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 extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and ethyl acetate is distilled off under reduced pressure. To the residue is added 35% ethanolic hydrochloric acid (0.5 ml), and the mixture is cooled and thereto is added diethyl ether (50 ml). The pricipitated white powder is separated by filtration to give the title compound (0.85 g).

Workup

  1. distillationis distilled off under reduced pressure
  2. customThe residue 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 under reduced pressure
  6. extractionthe residue is extracted with ethyl acetate
  7. washThe extract is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate, and ethyl acetate
  9. distillationis distilled off under reduced pressure
  10. additionTo the residue is added 35% ethanolic hydrochloric acid (0.5 ml)
  11. temperaturethe mixture is cooled
  12. additionis added diethyl ether (50 ml)
  13. customThe pricipitated white powder is separated by filtration

Sources & evidence

ORD record
ord-d5de0e2e45924b749f35c19965e020b1
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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