反应 #71997

反应方程式

Methyl chloroglyoxylate

triethylamine

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

→

title compound

收率 90.7%

Methyl cis(±)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetate

收率 90.7%

溶剂

ethyl acetate

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   洗涤washed with water and brine
3. 3
   干燥dried over anhydrous sodium sulfate
4. 4
   浓缩concentration under reduced pressure
5. 5
   其他the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0)

实验过程

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (200 mg, 0.593 mmol) was suspended in dichloromethane (5 mL). Methyl chloroglyoxylate (0.070 mL, 0.76 mmol), triethylamine (0.250 mL, 1.80 mmol) and DMAP (catalytic amount) were added under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0) to obtain 208.1 mg of the title compound as a colorless oily substance (91%).

来源