Triphenylphosphine → HCID 86731249, compound

Participants

Reaction Steps

To a solution of 2-(4-(benzyloxy)-3-fluorophenyl)-7-fluoro-1,3-benzoxazol-6-ol (1.13 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (0.841 g) and triphenylphosphine (1.26 g) in THF (20 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 2.52 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give a white solid. To the obtained solid was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate/methanol, and the solution was subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated, and the obtained solid was recrystallized (hexane/ethyl acetate) to give the title compound as white crystals (1.08 g).

Provenance & Evidence