Reaktion #47894

Reaktionsgleichung

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

N-hydroxy-benzotriazole

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

1,4-diaminobenzene

→

solid

Ausbeute 55.0%

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

Ausbeute 55.0%

Lösungsmittel

DMF

triethylamine

DMF

triethylamine

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle