반응 #453333

반응 방정식

N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

2-(((9-Fluorenyl)methoxycarbonyl)amino)acetic acid

N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride

→

({2-[2-(N-(tert-butoxycarbonyl)-N-methylamino)ethyl]phenylcarbamoyl}methyl)carbamic acid ((9-fluorenyl)methyl) ester

수율 95.6%

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 16 h, while it
2. 2
   온도was warming up to room temperature
3. 3
   세척washed with brine (100 ml)
4. 4
   추출The aqueous solution was extracted with dichloromethane (2×30 ml)
5. 5
   건조The combined organic layers were dried over magnesium sulfate
6. 6
   기타The solvent was removed in vacuo
7. 7
   기타The crude product was purified by flash chromatography on silica (80 g)

실험 절차

2-(((9-Fluorenyl)methoxycarbonyl)amino)acetic acid (2.49 g, 2.79 mmol) was suspended in dichloromethane (40 ml). The suspension was cooled to 0° C. N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (802 mg, 4.19 mmol) was added. The reaction mixture was stirred for 30 min at 0° C. A solution of N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (698 mg, 2.79 mmol) in dichloromethane (15 ml) was added. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was diluted with dichloromethane (100 ml) and washed with brine (100 ml). The aqueous solution was extracted with dichloromethane (2×30 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/heptane (1:1) as eluent, to give 1.412 g of ({2-[2-(N-(tert-butoxycarbonyl)-N-methylamino)ethyl]phenylcarbamoyl}methyl)carbamic acid ((9-fluorenyl)methyl) ester.

출처