Reaktion #81398

Reaktionsgleichung

S-(o-nitrophenyl)-D-cysteine

carbobenzyloxychloride

→

product

Ausbeute 94.1%

S-(o-Nitrophenyl)-N-carbobenzyloxy-D-cysteine

Ausbeute 94.1%

Lösungsmittel

NaOH

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe solution was then extracted with ether
2. 2
   workup.DISSOLUTIONThe resulting precipitate was dissolved in CH2Cl2
3. 3
   Trocknendried with Na2SO4
4. 4
   Sonstigeevaporated

Vorschrift

A solution of 11.60 g (48 mmol) of S-(o-nitrophenyl)-D-cysteine in 36 mL of 4N sodium hydroxide (NaOH) was cooled to 0° C. To this solution was added dropwise 6.85 mL (48 mmol) of carbobenzyloxychloride, and the mixture was stirred at room temperature for 2.5 hours. The pH was maintained at 10.8 with the addition of 4N NaOH as needed. The solution was then extracted with ether and the pH adjusted to 1.0 with 12N HCl. The resulting precipitate was dissolved in CH2Cl2, dried with Na2SO4 and evaporated to yield 17.0 g of product as a yellow gum. This material was used as is in the next reaction.

Quelle