Hydrochloric Acid → 3-[(2-Mercaptomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid

HRID 248669Notes

Reaction equation

HRID 248669 reaction equation
C([S:4][CH2:5][CH:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=O)C.[OH-].[Na+].Cl>CO>[SH:4][CH2:5][CH:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 156701493-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid

Product 1

HCID 156701503-[(2-Mercaptomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acidYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid (compound of Example 1) (1.7 g) is dissolved in methanol (9 ml), and thereto is added 1 N aqueous sodium hydroxide solution (9 ml) under nitrogen, and the mixture is stirred at room temperature for 30 minutes. The reaction mixture is adjusted to pH 1 by adding dropwise conc. hydrochloric acid, and 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 concentrated into dryness under reduced pressure to give the title compound (0.9 g).

Workup

  1. customthe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  2. additionThe fractions containing the desired compound
  3. customare collected
  4. concentrationconcentrated into dryness under reduced pressure

Sources & evidence

ORD record
ord-8b22fee49c724624866f452cb7e500ca
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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