反応 #535942

反応方程式

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

2-benzothiophenecarboxylic acid

1-aminocyclohexanecarboxylic acid phenylmethyl ester

1-hydroxybenzotriazole

→

title compound

収率 91.0%

1-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

収率 91.0%

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
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure, diethyl ether
8. 8
   workup.ADDITIONwas added to the obtained residue
9. 9
   workup.STIRRINGthe mixture was stirred overnight
10. 10
    ろ過The crystal was collected by filtration
11. 11
    温度heated
12. 12
    その他dried under reduced pressure

実験手順

Under ice-cooling, 5.9 g (31 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (28 mmol) of 2-benzothiophenecarboxylic acid, 6.5 g (28 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 4.5 g (29 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 solvent was distilled off under reduced pressure, diethyl ether was added to the obtained residue, and the mixture was stirred overnight. The crystal was collected by filtration and heated and dried under reduced pressure to obtain 10 g (91%) of the title compound.

出典