Hydrogen Peroxide → Nepsilon-dimethylamino-Nalpha-CBZ-O-t-butyl L-lysine N-oxide

Temperature

60 °C

A solution of 25.3 g of dimethylamine 2, 7.9 mL of 30% hydrogen peroxide and 150 mL of methanol was stirred for 5 h after which an additional 7.9 g of 30% hydrogen peroxide was added. The reaction was allowed to stir for 48 h and monitored by silica gel TLC, eluting with solvent A. A 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction was stirred for 7 h and another slurry of 5-10 mg platinum black added. The mixture was stirred overnight and monitored for peroxides using peroxide test paper with warming to 60° C. to remove peroxides when necessary. Once the reaction tested negative for peroxides, the mixture was filtered and concentrated. The residue was dissolved into 300 mL of EtOAc, dried over Na2SO4, filtered, concentrated and chromatographed on 400 g of silica gel, eluting with Solvent A to produce 13 g of product as a colorless oil.

1. additionwas added
2. washeluting with solvent A
3. additionA 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction
4. stirringwas stirred for 7 h
5. additionanother slurry of 5-10 mg platinum black added
6. stirringThe mixture was stirred overnight
7. customto remove peroxides when necessary
8. filtrationthe mixture was filtered
9. concentrationconcentrated
10. dissolutionThe residue was dissolved into 300 mL of EtOAc
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customchromatographed on 400 g of silica gel
15. washeluting with Solvent A

ORD record

ord-2d46e70de5c24d3e972efa60da2d0c9b

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05723619