Reaction #5538

Reaction equation

HCl

2-ethoxycarbonyl-5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine

NaOH

methanol

→

desired product

Yield 51.1%

2-carboxymethyl-5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine

Yield 51.1%

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISTILLATIONthe solvent was distilled off
3. 3
   workup.ADDITIONWater was added to the residue
4. 4
   Washthe resulting solid was washed with water
5. 5
   Otherdried

Procedure

To a solution of 2-ethoxycarbonyl-5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine (1.65 g, 4.62 mmoles) in methanol (5 ml) was added 1N NaOH (6.93 ml, 6.93 mmoles) and the mixture was stirred at room temperature for 2.5 hours. After the reaction mixture was washed with methylene chloride, 1N HCl (17.39 ml, 17.39 mmoles) was added thereto and the solvent was distilled off. Water was added to the residue and the resulting solid was washed with water and dried to obtain 777 mg of the desired product (51.1%, colorless solid).

Source