Diisopropylethylamine → N5-(2-chloro-5-sulfophenyl)-L-glutamine

Participants

Reaction Steps

To sodium 4-chloro-3-nitrobenzenesulfonate (1 mmol) were added 2 ml of methanol and 3 ml of water. A catalytic amount of 2% Pt-S/C was added to the mixture, followed by stirring at room temperature overnight in a hydrogen atmosphere. The catalyst was removed by filtration. After thoroughly drying, 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride, 163 mg (1.2 mmol) of HOAt, 456 mg (1.2 mmol) of HATU, 2 ml of DMF and 0.35 ml of DIEA were added and stirred at room temperature overnight. The reaction solution was diluted in water-acetonitrile and purified according to the purification step A to give the protected form of the title compound. The resulting protected product was dissolved in 3 ml of trifluoroacetic acid and stirred at room temperature for 2 hours. The solvent was then removed by distillation. The mixture was purified according to the purification step A to give the title compound.

Provenance & Evidence