Reaktion #574066

Reaktionsgleichung

N-(2-mercapto-2-methylpropionyl)-L-cysteine

dicyclohexylcarbodiimide

Dimethylamine hydrochloride

triethylamine

→

titled compound

Ausbeute 98.9%

N-(2-Mercapto-2-Methylpropionyl)-L-Cysteine N,N-Dimethylamide

Ausbeute 98.9%

Lösungsmittel

methylene chloride

methylene chloride

ethylacetate

methylene chloride

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.ADDITIONwas added dropwise under ice-
4. 4
   Temperaturcooling
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 15 minutes under ice-
6. 6
   Temperaturcooling and 3 hours at room temperature
7. 7
   Filtrationfiltered
8. 8
   WaschenThe organic layer was washed with water
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe oily residue was purified by a silica gel column chromatography

Vorschrift

To a stirred solution of N-(2-mercapto-2-methylpropionyl)-L-cysteine (1.0 g) in methylene chloride(4 ml), dicyclohexylcarbodiimide (0.5 g) dissolved in methylene chloride(4 ml) was added dropwise. After the addition, the reaction mixture was stirred for 30 minutes under ice cooling and for 1 hour at room temperature. Dimethylamine hydrochloride(0.2 g) and triethylamine(0.4 ml) dissolved in a mixture of methylene chloride (2 ml) and methanol(1 ml) was added dropwise under ice-cooling. The reaction mixture was stirred for 15 minutes under ice-cooling and 3 hours at room temperature. To the reaction mixture, ethylacetate was added and filtered. The organic layer was washed with water and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.6 g(50%) of the titled compound.

Quelle