تفاعل #5677

معادلة التفاعل

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

المردود 121.2%

المذيبات

acetic acid

methanol

chloroform

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر