反应 #1272

反应方程式

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

溶剂

methanol

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   洗涤eluting 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
   其他to remove peroxides when necessary
8. 8
   过滤the mixture was filtered
9. 9
   浓缩concentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved into 300 mL of EtOAc
11. 11
    干燥dried over Na2SO4
12. 12
    过滤filtered
13. 13
    浓缩concentrated
14. 14
    其他chromatographed on 400 g of silica gel
15. 15
    洗涤eluting with Solvent A

实验过程

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.

来源