Sodium Hydroxide → 2-((3-methyl-4-(2-(N-benzyl-N-carboxymethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

HRID 52154Notes

Reaction equation

HRID 52154 reaction equation
[CH3:1][C:2]1[C:3]([CH2:25][S:26][C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][C:13]([O:15]CC)=[O:14].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:3]([CH2:25][S:26][C:27]2[NH:28][C:29]3[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=3[N:31]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 199630622-((3-Methyl-4-(2-(N-benzyl-N-ethoxycarbonylmethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

Product 1

HCID 199631092-((3-methyl-4-(2-(N-benzyl-N-carboxymethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-((3-Methyl-4-(2-(N-benzyl-N-ethoxycarbonylmethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole (1.0 g) was dissolved in ethanol (10 ml) and thereto was added an aqueous solution (3 ml) of 1N sodium hydroxide. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and adjusted to pH 4 with an aqueous solution of dilute acetic acid. The resultant crystals were collected by filtration to give 2-((3-methyl-4(2-(N-benzyl-N-carboxymethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe resultant crystals were collected by filtration

Sources & evidence

ORD record
ord-58e6b3aed1a040e5a365ffe63a3da825
Source dataset
uspto-grants-1997_04
Patent number
US05616581

Reaction notes

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