反応 #47894

反応方程式

4-(tert-butoxycarbonylamino-methyl)-benzoic acid

N-hydroxy-benzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

1,4-diaminobenzene

→

solid

収率 55.0%

[4-(4-Amino-phenylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester

収率 55.0%

溶媒

DMF

triethylamine

DMF

triethylamine

反応条件

後処理

1. 1
   その他After completion of the chemical reaction the mixture
2. 2
   その他is evaporated at high vacuum
3. 3
   その他the residue is partitioned between ethyl acetate
4. 4
   乾燥The organic phase is dried over sodium sulfate
5. 5
   その他the crude product is purified by silica gel flash chromatography

実験手順

To a solution of 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (1.005 g) and N-hydroxy-benzotriazole (HOBt)(0.642 g) in DMF (30 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)(2.76 g) and triethylamine (2.005 ml). The mixture is stirred for 1 h at ambient temperature. This solution is added at 0° C. slowly to a solution of 1,4-diaminobenzene (0.43 g) and triethylamine (0.45 ml) in DMF (5 ml). After completion of the chemical reaction the mixture is evaporated at high vacuum and the residue is partitioned between ethyl acetate and an aqueous saturated sodium bicarbonate solution. The organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A colorless solid (0.735 g) is obtained in 55% yield.

出典