반응 #1272

반응 방정식

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

용매

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   세척eluting 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
   기타to remove peroxides when necessary
8. 8
   여과the mixture was filtered
9. 9
   농축concentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved into 300 mL of EtOAc
11. 11
    건조dried over Na2SO4
12. 12
    여과filtered
13. 13
    농축concentrated
14. 14
    기타chromatographed on 400 g of silica gel
15. 15
    세척eluting with Solvent A

실험 절차

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.

출처