反応 #161038

反応方程式

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

4-(chloromethyl)benzoic acid

1-aminocyclohexanecarboxylic acid methyl ester hydrochloride

triethylamine

1-hydroxybenzotriazole

→

title compound

収率 53.0%

1-[[[4-(Chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester

収率 53.0%

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度Under ice-cooling
2. 2
   workup.DISTILLATIONthe reaction solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONWater was added to the residue
4. 4
   抽出the mixture was extracted with ethyl acetate twice
5. 5
   洗浄The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
6. 6
   乾燥a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate
7. 7
   その他The obtained residue was purified by silica gel column chromatography

実験手順

Under ice-cooling, 9.96 g (52 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 8.8 g (52 mmol) of 4-(chloromethyl)benzoic acid, 10 g (52 mmol) of 1-aminocyclohexanecarboxylic acid methyl ester hydrochloride, 15 g (152 mmol) of triethylamine and 8.63 g (56 mmol) of 1-hydroxybenzotriazole in methylene chloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography to obtain 8.5 g (53%) of the title compound.

出典