반응 #78573

반응 방정식

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

수율 78.0%

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

수율 78.0%

용매

tetrahydrofuran

water

반응 조건

후처리

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
   추출the resulting solution was extracted three times with 20 mL of dichloromethane
4. 4
   건조The extracts were dried over sodium sulfate
5. 5
   기타evaporated down

실험 절차

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.

출처