反応 #40872

反応方程式

water

N-(4-bromobenzyl)-L-valine

sodium bicarbonate

valeroyl chloride

→

N-(4-bromobenzyl)-N-valeryl-L-valine

収率 91.2%

溶媒

THF

反応条件

後処理

1. 1
   workup.WAITis left
2. 2
   workup.ADDITIONis added over a period of 15 min
3. 3
   workup.WAITThe mixture is then left
4. 4
   その他to react at 20-25° C. for 3 h
5. 5
   workup.DISTILLATIONthe THF is distilled at low pressure
6. 6
   workup.DISTILLATIONthe remains of THF distilled off completely
7. 7
   その他The solid obtained
8. 8
   ろ過is filtered
9. 9
   洗浄washed with 50 mL of water
10. 10
    その他dried in a vacuum over

実験手順

A mixture made up of 5 g (17.47 mmol) of N-(4-bromobenzyl)-L-valine and 5.9 g (70.24 mmol) of sodium bicarbonate in 50 mL of dry THF is left under stirring and under nitrogen atmosphere for one hour. The preceding suspension is cooled to 0° C. and to it is added over a period of 15 min. 4.2 mL (35.41 mmol) of valeroyl chloride. The mixture is then left to react at 20-25° C. for 3 h, 50 mL of water is added and the THF is distilled at low pressure. The resulting solution is taken to pH 2 with HCl 35% and the remains of THF distilled off completely. The solid obtained is filtered, washed with 50 mL of water and dried in a vacuum over to provide 5.9 g (91.2%) of N-(4-bromobenzyl)-N-valeryl-L-valine. The solid is recrystallised from a mixture of EtOH/H2O 2:1. M.p.=123° C.

出典