Reaktion #2375302

Reaktionsgleichung

Bromacetic acid

N'-benzyloxycarbonyl-L-lysine

bromacetic acid

→

Nα,Nα -bis (carboxymethyl)-L-lysine

Lösungsmittel

sodium hydroxide

NaOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling bath
2. 2
   Sonstigethe cooling bath was removed
3. 3
   workup.STIRRINGthe solution was stirred overnight at room temperature
4. 4
   TemperaturThe solution was then heated for two hours at 50° C.
5. 5
   workup.ADDITION300 ml of 1 M hydrochloric acid (HCl) was added dropwise
6. 6
   TemperaturThe mixture was then cooled to room temperature
7. 7
   Sonstigeto precipitate
8. 8
   FiltrationThe Z-NTA was collected by filtration
9. 9
   Sonstigefurther purified
10. 10
    workup.DISSOLUTIONby dissolving in 1 M NaOH
11. 11
    Sonstigere-precipitating with the same amount of 1 M HCl
12. 12
    Filtrationfiltering
13. 13
    SonstigeThe dissolving and precipitating cycle

Vorschrift

Bromacetic acid (28 g, 200 mmole) was dissolved in 100 ml of 2 M sodium hydroxide (NaOH) and cooled to 0° C. A solution of 28 g (100 mmole) of N'-benzyloxycarbonyl-L-lysine in 150 ml of 2 M NaOH was slowly added dropwise into the bromacetic acid solution while stirring in a 0° C. cooling bath. After 2 hours, the cooling bath was removed and the solution was stirred overnight at room temperature. The solution was then heated for two hours at 50° C. and 300 ml of 1 M hydrochloric acid (HCl) was added dropwise. The mixture was then cooled to room temperature allowing the N'-benzyloxycarbonyl-nitrilotriacetic acid (Z-NTA) to precipitate. The Z-NTA was collected by filtration and further purified by dissolving in 1 M NaOH, re-precipitating with the same amount of 1 M HCl and filtering. The dissolving and precipitating cycle was repeated twice.

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