Hydrochloric Acid → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% in mineral oil, 2.88 g, 72 mmol) in DMF (25 mL) at 0° C. was added (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (7 g, 34 mmol) in DMF (25 mL). After 2 h 1-fluoro-2-nitrobenzene (5.29 g, 37.5 mmol) in DMF (25 mL) was added and the resulting mixture stirred for 3 h at 0° C. The mixture was poured into ice/H2O (200 mL), acidified to pH 5.0 with 1 N HCl and extracted with EtOAc. The combined extracts were dried over Na2SO4, concentrated and purified by flash chromatography to give (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenoxy)-propionic acid (10.9 g, 97%).

Provenance & Evidence