تفاعل #47894

معادلة التفاعل

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

N-hydroxy-benzotriazole

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

1,4-diaminobenzene

→

solid

المردود 55.0%

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

المردود 55.0%

المذيبات

DMF

triethylamine

DMF

triethylamine

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر