Hydrochloric Acid → HCID 15670201, compound

HRID 248684Notes

Reaction equation

HRID 248684 reaction equation
C([S:4][CH2:5][CH:6]([CH2:19][CH:20]1[O:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:21]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][CH:20]1[O:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:21]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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15670195HCID 15670195, compound

Product 1

HCID 15670201HCID 15670201, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-[[2-Acetylthiomethyl-3-(4-benzyl-2-morpholinyl)-propionyl]amino]benzoic acid (compound of Example 47) (1.0 g) is dissolved in 50% aqueous methanol (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 4.5 with 10% hydrochloric acid, and methanol is distilled off under reduced pressure. The residue is extracted with ethyl acetate, and 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 (0.3 g).

Workup

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

Sources & evidence

ORD record
ord-eead5bb8894740669b2603ae81207dec
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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