反応 #161001

反応方程式

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

1-aminocyclohexanecarboxylic acid methyl ester hydrochloride

1-hydroxybenzotriazole

3-furancarboxylic acid

triethylamine

→

title compound

収率 91.0%

1-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acid methyl ester

収率 91.0%

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度cooling
2. 2
   濃縮the reaction solution was concentrated under reduced pressure
3. 3
   workup.ADDITIONEthyl acetate was added to the residue
4. 4
   洗浄the mixture was successively washed with water
5. 5
   乾燥by drying with anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure
7. 7
   洗浄the obtained crystal was washed with diisopropyl ether

実験手順

105 g (550 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 98.8 g (500 mmol) of 1-aminocyclohexanecarboxylic acid methyl ester hydrochloride, 84.2 g (550 mmol) of 1-hydroxybenzotriazole, 56.0 g (500 mmol) of 3-furancarboxylic acid and 152 g (1.5 mol) of triethylamine in 1000 ml of methylene chloride under ice-cooling. After the mixture was stirred at room temperature overnight, the reaction solution was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained crystal was washed with diisopropyl ether to obtain 114 g (91%) of the title compound.

出典