Ammonium Chloride → 4-[4-((S)-1-{[2-(4-amino-2-chloro-5-methoxy-phenyl)-ethyl]-tert-butoxycarbonyl-amino}ethyl)-phenyl]piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[4-((S)-1-{tert-butoxycarbonyl-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]amino}-ethyl)phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.32 g, 0.53 mmol) in methanol (12 mL), a saturated solution of NH4Cl (8 mL) and zinc powder (0.175 g, 2.66 mmol) were added at room temperature and the reaction was stirred at 80° C. for 2 hours. The mixture was allowed to cool to room temperature and then filtered through cotton wool. Water (50 mL) was added and the mixture extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.28 g, 89%) which was used without further purification.

Provenance & Evidence