Ammonium Chloride → (S)-3-(2-amino-6-bromophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

Participants

Reaction Steps

A mixture of (S)-3-(2-bromo-6-nitrophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (2.1 g, 5.18 mmol), zinc dust (3.39 g, 51.8 mmol) and NH4Cl (2.77 g, 51.8 mmol) in MeOH/THF 1:1 (40 mL) was stirred at RT until TLC indicated the reaction was complete. The mixture was then filtered and the filtrate concentrated. The residue was mixed with H2O/EtOAc (50 mL/50 mL) and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated to afford (S)-3-(2-amino-6-bromophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (1.88 g, 97%) as an off-white foam which was used without purification.

Provenance & Evidence