Reacción #642206

Ecuación de reacción

cesium

Boc-arginine

benzyl bromide

Boc-Arg-OH

Cs2CO3

→

H-Arg-OBzl

Disolventes

water

DMF

methanol

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated in vacuo to dryness
2. 2
   OtroResidual water was removed
3. 3
   workup.ADDITIONaddition and evaporation of toluene
4. 4
   OtroThe DMF was removed in vacuo
5. 5
   workup.DISSOLUTIONthe product was dissolved in acetone
6. 6
   Filtraciónfiltered
7. 7
   OtroThe filtrate was evaporated in vacuo
8. 8
   workup.ADDITIONthe product was treated with 95% trifluoroactetic acid (TFA) (4 ml)

Procedimiento

Water (2 ml) was added to a solution of Boc-Arg-OH (2.5 mmol) in methanol (20 ml). The solution was neutralised with a 20% solution of Cs2CO3 in water and then evaporated in vacuo to dryness. Residual water was removed by repeated addition and evaporation of toluene. The solid cesium salt of Boc-arginine was treated with DMF (25 ml) and benzyl bromide (3 mmol) and stirred at room temperature for 6 h. The DMF was removed in vacuo and the product was dissolved in acetone and filtered. The filtrate was evaporated in vacuo and the product was treated with 95% trifluoroactetic acid (TFA) (4 ml). The resulting product H-Arg-OBzl was isolated by tituration by diethyl ether. The salt of H-Arg-OBzl was isolated by treating the product with para-toluenesulfonic acid (5 mmol) in ether.

Fuente