Reacción #1272

Ecuación de reacción

dimethylamine

Nε-dimethylamino-Nα-CBZ-O-t-butyl L-lysine

hydrogen peroxide

hydrogen peroxide

→

product

Nε-dimethylamino-Nα-CBZ-O-t-butyl L-lysine N-oxide

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Lavadoeluting with solvent A
3. 3
   workup.ADDITIONA 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction
4. 4
   workup.STIRRINGwas stirred for 7 h
5. 5
   workup.ADDITIONanother slurry of 5-10 mg platinum black added
6. 6
   workup.STIRRINGThe mixture was stirred overnight
7. 7
   Otroto remove peroxides when necessary
8. 8
   Filtraciónthe mixture was filtered
9. 9
   Concentraciónconcentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved into 300 mL of EtOAc
11. 11
    Secadodried over Na2SO4
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónconcentrated
14. 14
    Otrochromatographed on 400 g of silica gel
15. 15
    Lavadoeluting with Solvent A

Procedimiento

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.

Fuente