反应 #1269895

反应方程式

[(2-amino-5-chloro-benzyl)-tert-butoxycarbonyl-amino]-acetic acid ethyl ester

potassium tert-butoxide

water

ammonium chloride

→

title compound

收率 88.0%

7-Chloro-2-oxo-1,2,3,5-tetrahydro-benzo[1,4]diazepine-4-carboxylic acid tert-butyl ester

收率 88.0%

溶剂

tetrahydrofuran

ethyl acetate

反应条件

后处理

1. 1
   workup.ADDITIONaddition the cooling bath
2. 2
   其他was removed
3. 3
   其他reaction mixture
4. 4
   过滤After 10 min the precipitate was collected by filtration
5. 5
   其他The organic layer was separated from the filtrate
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated in vacuo
8. 8
   过滤had previously been collected by filtration
9. 9
   其他crystallized from hot ethyl acetate

实验过程

To a solution of [(2-amino-5-chloro-benzyl)-tert-butoxycarbonyl-amino]-acetic acid ethyl ester (60 g, 0.18 mol) in tetrahydrofuran (600 ml) was added potassium tert-butoxide (22 g, 0.19 mol) in small portions at 5° C. under cooling on an ice-water batch. After completed addition the cooling bath was removed and reaction mixture was stirred for 3 h at room temperature followed by addition of water (400 ml), saturated aqueous ammonium chloride solution (280 ml) and ethyl acetate (800 ml). After 10 min the precipitate was collected by filtration. The organic layer was separated from the filtrate, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was combined with the precipitate, which had previously been collected by filtration, and crystallized from hot ethyl acetate to give the title compound (46 g, 88%) as white solid. MS m/e: 295 (M−H+).

来源