Реакция #5677

Уравнение реакции

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

dimethylaminopyridine

dimethylaminopyridine hydrochloride

N-tert-butoxycarbonyl-L-methionine

dicyclohexylcarbodiimide

→

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

Выход 121.2%

Растворители

acetic acid

methanol

chloroform

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 30 minutes
2. 2
   ДругоеThe insoluble materials are removed by filtration
3. 3
   workup.ADDITIONto the filtrate is added 5% aqueous sodium hydrogen sulfate solution
4. 4
   Экстракцияthe mixture is extracted with dichloromethane
5. 5
   ПромывкаThe dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   ДругоеThe solvent is evaporated
8. 8
   Другоеthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=150:1)

Методика

5-Hydroxy-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.7 g), dimethylaminopyridine (0.83 g) and dimethylaminopyridine hydrochloride (0.72 g) are dissolved in chloroform (15 ml), and thereto are added N-tert-butoxycarbonyl-L-methionine (0.56 g) and dicyclohexylcarbodiimide (0.93 g), and the mixture is stirred at room temperature for 3 hours. To the mixture are added methanol (3 ml) and acetic acid (0.7 ml), and the mixture is stirred at room temperature for 30 minutes. The insoluble materials are removed by filtration, and to the filtrate is added 5% aqueous sodium hydrogen sulfate solution, and the mixture is extracted with dichloromethane. The dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent is evaporated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=150:1) to give 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.27 g).

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