Potassium Carbonate → (R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid

Participants

Reaction Conditions

Reaction Steps

(R)-2-tert-Butoxycarbonylamino-3-aminopropionic acid (5 g) and potassium carbonate (6.77 g) were added to a solution of 2-fluoronitrobenzene (3.45 g) in N,N-dimethylformamide (60 ml), and the mixture was stirred overnight at 70° C. After the reaction mixture was allowed to cool, the reaction mixture was poured into ice-water and washed with ethyl acetate. The water layer was adjusted to pH 3 with 1N hydrochloric acid, extracted with ethyl acetate. This organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the residue for crystallization, collected by filtration,to thereby obtain 7.9 g of the title compound (Yield 99%).

Provenance & Evidence