Reaction #1824320

Reaction equation

2,5-dithia cyclohexanone

cysteine decyl ester hydrochloride

triethyl amine

→

S-(2-mercaptoethyl)-N-(2-mercapto-1(decyloxycarbonyl)-ethyl)-mercaptoacetamide

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONare added
2. 2
   Washwashed three times with 2% aqueous citric acid, saturated sodium hydrogencarbonate solution
3. 3
   DryingAfter drying above sodium sulfate
4. 4
   Otherthe solvent is evaporated under reduced pressure
5. 5
   OtherThe oily residue is crystallized by trituration with diethyl ether

Procedure

13.42 g (0.1 mol) of 2,5-dithia cyclohexanone dissolved in 250 ml of anhydrous dichloromethane are added by dropping, and in an argon atmosphere, to a solution of 29.79 g (0.1 mol) of cysteine decyl ester hydrochloride and 10.12 g (0.1 mol) of triethyl amine in 500 ml of anhydrous dichloromethane. The reaction mixture is kept agitated overnight at room temperature and then washed three times with 2% aqueous citric acid, saturated sodium hydrogencarbonate solution and with water. After drying above sodium sulfate, the solvent is evaporated under reduced pressure. The oily residue is crystallized by trituration with diethyl ether.

Source