Bromoacetic Acid → N-(5-Amino-1-carboxypentyl)iminodiacetic acid

Temperature

0 °C

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.

1. temperaturecooling bath
2. customthe cooling bath was removed
3. stirringthe solution was stirred overnight at room temperature
4. temperatureThe solution was then heated for two hours at 50° C.
5. addition300 ml of 1 M hydrochloric acid (HCl) was added dropwise
6. temperatureThe mixture was then cooled to room temperature
7. customto precipitate
8. filtrationThe Z-NTA was collected by filtration
9. customfurther purified
10. dissolutionby dissolving in 1 M NaOH
11. customre-precipitating with the same amount of 1 M HCl
12. filtrationfiltering
13. customThe dissolving and precipitating cycle

ORD record

ord-98f200f7ee1649548d566e7161107936

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06087452