Hydrochloric Acid → HCID 67077060, compound

Participants

Reaction Conditions

Reaction Steps

A solution of BOC-Ser-OH (2.58 g, 12.6 mmol) in DMF (10.00 mL) was added to a suspension of NaH (60% in mineral oil, 1.06 g, 26.4 mmol) in DMF (10 mL) at 0° C. over 10 min. After 1 h at 0° C. a solution of 1,2-difluoro-3-nitrobenzene (2 g, 12.6 mmol) in DMF (10 mL) was added and the mixture stirred at 0° C. for 2 h. The mixture was diluted with H2O and acidified to pH 3 with 1 N HCl, then extracted with EtOAc. The combined extracts were dried over MgSO4 and the filtrate was concentrated to give a residue that was purified by silica gel chromatography to afford (S)-2-(tert-butoxycarbonylamino)-3-(2-fluoro-6-nitrophenoxy)propanoic acid (2.94 g, 68%) as a yellow foam.

Provenance & Evidence