Reaction #2383767

Reaction equation

N,N-bis-(tert-butoxycarboxy-methyl)-2-bromoethylamine

diisopropylethylamine

ethylmercaptan

→

N,N-Bis-(tert-butoxycarboxy-methyl)-S-ethyl-2-mercaptoethylamine

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is refluxed overnight
2. 2
   ExtractionThen, the solution is extracted twice with semi-saturated, aqueous sodium bicarbonate solution
3. 3
   OtherThe organic phase is dried on sodium sulfate
4. 4
   Otherthe solvent is evaporated in a vacuum
5. 5
   OtherThe residue is chromatographed on silica gel (eluant: dichloromethane/methanol 99:1)

Procedure

3.52 g (10 mmol) of N,N-bis-(tert-butoxycarboxy-methyl)-2-bromoethylamine is dissolved in 50 ml of absolute dichloromethane and mixed with 1.29 g (10 mmol) of diisopropylethylamine and 0.621 g (10 mmol) of ethylmercaptan. The reaction mixture is refluxed overnight. Then, the solution is extracted twice with semi-saturated, aqueous sodium bicarbonate solution. The organic phase is dried on sodium sulfate, and the solvent is evaporated in a vacuum. The residue is chromatographed on silica gel (eluant: dichloromethane/methanol 99:1).

Source