反応 #1272

反応方程式

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

溶媒

methanol

反応条件

後処理

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

実験手順

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.

出典