Reaktion #535942

Reaktionsgleichung

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

2-benzothiophenecarboxylic acid

1-aminocyclohexanecarboxylic acid phenylmethyl ester

1-hydroxybenzotriazole

→

title compound

Ausbeute 91.0%

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

Ausbeute 91.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder 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
   Extraktionthe mixture was extracted with ethyl acetate twice
5. 5
   WaschenThe obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
6. 6
   Trocknena 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
    FiltrationThe crystal was collected by filtration
11. 11
    Temperaturheated
12. 12
    Sonstigedried under reduced pressure

Vorschrift

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.

Quelle