Reaction #47894

Reaction equation

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

N-hydroxy-benzotriazole

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

1,4-diaminobenzene

→

solid

Yield 55.0%

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

Yield 55.0%

Solvents

DMF

triethylamine

DMF

triethylamine

Conditions

Workup

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

Procedure

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.

Source