L-Lysine → 2-Amino-6-benzamidohexanoic acid

Temperature

0 °C

To a solution of L-lysine (1) (3.65 g, 0.02 mol) in water (50 mL) at 90° C. was added CuCO3 (2.5 g) portionwise. After being refluxed for 40 min, the mixture was cooled and filtered. The filtrate was further cooled to 0° C., and a solution of BzCl (3.5 mL, 0.03 mol) and NaOH (2.7 g, 0.0685 mol) in water (20 mL) were added. The reaction was stirred at 0° C. for 1 h and then allowed to warm to room temperature. After 2 days, the reaction mixture was filtered and the solid was washed with water and Et2O. This obtained solid was then added to a solution of EDTA (7.0 g) in water (350 mL), the mixture was heated to reflux until the reaction solution became clear blue. The reaction was cooled which gave a white precipitate. This precipitate was collected and washed with water and Et2O and dried which afforded the title compound as a white solid (1.8 g, 36%).

1. temperatureAfter being refluxed for 40 min
2. temperaturethe mixture was cooled
3. filtrationfiltered
4. temperatureto warm to room temperature
5. waitAfter 2 days
6. filtrationthe reaction mixture was filtered
7. washthe solid was washed with water and Et2O
8. additionThis obtained solid was then added to a solution of EDTA (7.0 g) in water (350 mL)
9. temperaturethe mixture was heated
10. temperatureto reflux until the reaction solution
11. temperatureThe reaction was cooled which
12. customgave a white precipitate
13. customThis precipitate was collected
14. washwashed with water and Et2O
15. customdried which

ORD record

ord-5029d6fbfb3f42ef8273e1ec66792115

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022092B2