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

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.

1. temperatureUnder ice-cooling
2. distillationthe reaction solvent was distilled off under reduced pressure
3. additionWater was added to the residue
4. extractionthe mixture was extracted with ethyl acetate twice
5. washThe obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate
7. distillationThe solvent was distilled off under reduced pressure, diethyl ether
8. additionwas added to the obtained residue
9. stirringthe mixture was stirred overnight
10. filtrationThe crystal was collected by filtration
11. customheated/dried under reduced pressure

ORD 기록

ord-3f8e2bf61c354e568d0daf7c0bd00327

출처 데이터셋

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08829209B2