반응 #83024

반응 방정식

5-hydroxy-7-chloro-1-[2-methoxy-4-(2methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

dimethylaminopyridine

dimethylaminopyridine hydrochloride

acetic acid

N-tert-butoxy-carbonyl-L-methionine

dicyclohexylcarbodi-imide

→

5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine

용매

chloroform

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   기타The resulting insolubles were removed by filtration
3. 3
   workup.ADDITIONThe filtrate was mixed with a 5% aqueous sodium hydrogensulfate solution
4. 4
   추출followed by extraction with dichloromethane
5. 5
   세척The dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution
6. 6
   건조a saturated aqueous sodium chloride solution in this order and dried over magnesium sulfate
7. 7
   농축The resulting dichloromethane solution was concentrated for solvent removal
8. 8
   기타The residue was purified by silica gel column chromatography [elutant: dichloromethane/methanol=150/1]

실험 절차

In 15 ml of chloroform were dissolved 0.7 g of 5-hydroxy-7-chloro-1-[2-methoxy-4-(2methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine, 0.83 g of dimethylaminopyridine and 0.72 g of dimethylaminopyridine hydrochloride. Thereto were added 0.56 g of N-tert-butoxy-carbonyl-L-methionine and 0.93 g of dicyclohexylcarbodi-imide. The mixture was stirred at room temperature for 3 hours. 3 ml of methanol and 0.7 ml of acetic acid were added, and the mixture was stirred at room temperature for 30 minutes. The resulting insolubles were removed by filtration. The filtrate was mixed with a 5% aqueous sodium hydrogensulfate solution, followed by extraction with dichloromethane. The dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution in this order and dried over magnesium sulfate. The resulting dichloromethane solution was concentrated for solvent removal. The residue was purified by silica gel column chromatography [elutant: dichloromethane/methanol=150/1] to obtain 1.27 g of 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine.

출처