反応 #5677

反応方程式

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

収率 121.2%

溶媒

acetic acid

methanol

chloroform

反応条件

後処理

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

実験手順

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).

出典