Reaction #2383771

Reaction equation

methylene chloride

diisopropylethylamine

bis-(2-methylthioethyl)-amine

bromoacetic acid methyl ester

→

N,N-bis-(2-methylthioethyl)-glycine methyl ester

Solvents

acetonitrile

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONis added in drops under a cover-gas atmosphere
2. 2
   Washwashed twice with saturated sodium bicarbonate solution
3. 3
   DryingThe organic phase is dried with sodium sulfate
4. 4
   Concentrationconcentrated by evaporation
5. 5
   Otherthe residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol

Procedure

165 mg of bis-(2-methylthioethyl)-amine (Example 8b) is dissolved in 20 ml of acetonitrile and mixed with 174 μl of diisopropylethylamine. 92.7 μl of bromoacetic acid methyl ester, dissolved in 20 ml of acetonitrile, is added in drops under a cover-gas atmosphere, and the batch is stirred for 18 hours at room temperature. The acetonitrile is drawn off, the residue is taken up with methylene chloride and washed twice with saturated sodium bicarbonate solution. The organic phase is dried with sodium sulfate and concentrated by evaporation, and the residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol: Yield 183 mg=77% of theory.

Source