Reaktion #214475

Reaktionsgleichung

N-(2-Mercapto-2-methylpropanoyl)-L-cysteine

pivaloyl chloride

hydrochloric acid

→

S-pivaloyl-N-(S-pivaloyl-2-mercapto-2-methylpropanoyl)-L-cysteine

Ausbeute 16.4%

Lösungsmittel

sodium hydroxide

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added dropwise at 0° C.
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe mixture is stirred for 1 hour at room temperature
4. 4
   ExtraktionThe produced oil is extracted with ethyl acetate
5. 5
   Waschenthe organic layer is washed with water
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated to dryness under reduced pressure

Vorschrift

N-(2-Mercapto-2-methylpropanoyl)-L-cysteine (11.2 g, 0.05 mol) is dissolved in N sodium hydroxide (50 ml) and pivaloyl chloride (17.0 g, 0.13 mol) and aqueous N sodium hydroxide (150 ml) are added dropwise at 0° C. with stirring under a nitrogen atmosphere. After the addition, the mixture is stirred for 1 hour at room temperature and acidified with 6 N hydrochloric acid. The produced oil is extracted with ethyl acetate and the organic layer is washed with water, dried and concentrated to dryness under reduced pressure to yield 3.2 g (16.4%) of S-pivaloyl-N-(S-pivaloyl-2-mercapto-2-methylpropanoyl)-L-cysteine.

Quelle