反応 #453333

反応方程式

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

収率 95.6%

溶媒

dichloromethane

dichloromethane

dichloromethane

反応条件

後処理

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

実験手順

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.

出典