تفاعل #78573

معادلة التفاعل

1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride

potassium carbonate

n-hexyl chloroformate

→

crude product

المردود 78.0%

1-Methyl-2-[N-[4-(N-n-hexyloxycarbonylamidino)phenyl]aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

المردود 78.0%

المذيبات

tetrahydrofuran

water

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONThe solvent was then distilled off
2. 2
   workup.ADDITIONthe residue was mixed with about 50 mL of saturated saline solution
3. 3
   استخلاصthe resulting solution was extracted three times with 20 mL of dichloromethane
4. 4
   تجفيفThe extracts were dried over sodium sulfate
5. 5
   أخرىevaporated down

الإجراء التجريبي

1.1 g (2.06 mmol) of 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride was dissolved in a mixture of 40 mL of tetrahydrofuran and 10 mL of water, then 570 mg (4.12 mmol) of potassium carbonate and 362 mg (2.2 mmol) of n-hexyl chloroformate were added and stirred for two hours at room temperature. The solvent was then distilled off, the residue was mixed with about 50 mL of saturated saline solution and the resulting solution was extracted three times with 20 mL of dichloromethane. The extracts were dried over sodium sulfate and evaporated down. The crude product thus obtained was purified by column chromatography (100 g silica gel; dichloromethane+5% ethanol). Yield: 78% of theory, C35H42N6O5 (626.8); Rf value: 0.49 (silica gel; dichloromethane/ethanol=19:1); EKA mass spectrum: (M+H)+=627; (M+H+Na)++=325; (M+2H)++=314.

المصدر