反応 #78573

反応方程式

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

収率 78.0%

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

収率 78.0%

溶媒

tetrahydrofuran

water

反応条件

後処理

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
   抽出the resulting solution was extracted three times with 20 mL of dichloromethane
4. 4
   乾燥The extracts were dried over sodium sulfate
5. 5
   その他evaporated down

実験手順

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.

出典