Reaction #2383769

Reaction equation

S-methyl-thioglycolic acid

N-hydroxysuccinimide

2-methylthio-ethylamine

dicyclohexylcarbodiimide

→

S-methyl-thioglycolic Acid-N-(2-methylthioethyl)-amide

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   FiltrationThe precipitate is filtered off
2. 2
   Washthe filtrate is washed twice with semi-saturated sodium bicarbonate solution and once with water
3. 3
   Dryingdried 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

6 ml of 2-methylthio-ethylamine is dissolved in 250 ml of methylene chloride, mixed with 6.84 g of S-methyl-thioglycolic acid and with 7.42 g of N-hydroxysuccinimide and mixed drop by drop with 13.3 g of dicyclohexylcarbodiimide in 250 ml of methylene chloride under a cover-gas atmosphere. It is stirred, for 3 more hours at room temperature. The precipitate is filtered off, the filtrate is washed twice with semi-saturated sodium bicarbonate solution and once with water, dried with sodium sulfate and concentrated by evaporation. The residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol: Yield 10 g=86.7% of theory.

Source