4-Nitrobenzoic Acid → [(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoate

Participants

Reaction Steps

Diisopropyl azodicarboxylate (6 ml) was added dropwise to a solution of tert-butyl [(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate (5.88 g), 4-nitrobenzoic acid (4.84 g), and triphenylphosphine (7.59 g) in THF (100 ml) under ice-cooling in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for two hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3). Then, the resulting powder was triturated with toluene-hexane to obtain 6.69 g of the title compound.

Provenance & Evidence