Reacción #47894

Ecuación de reacción

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

N-hydroxy-benzotriazole

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

1,4-diaminobenzene

→

solid

Rendimiento 55.0%

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

Rendimiento 55.0%

Disolventes

DMF

triethylamine

DMF

triethylamine

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente