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

HRID 1646279Notes

Reaction equation

HRID 1646279 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 1N 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-ba8be9a0a64c451aad627b852895108d
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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