반응 #161035

반응 방정식

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

2-benzothiophenecarboxylic acid

1-aminocyclohexanecarboxylic acid phenylmethyl ester

1-hydroxybenzotriazole

→

title compound

수율 91.0%

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

수율 91.0%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도Under 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
   추출the mixture was extracted with ethyl acetate twice
5. 5
   세척The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
6. 6
   건조a 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
    여과The crystal was collected by filtration
11. 11
    기타heated/dried under reduced pressure

실험 절차

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/dried under reduced pressure to obtain 10 g (91%) of the title compound.

출처