3-Butyn-1-OL → (R)-3-(3-fluoro-4-iodophenyl)-5-((4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

Participants

Reaction Steps

In Ar atmosphere, (R)-5-(azidomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one (WO 2003022824 or F. Reck, et al. J. Med. Chem. 2007, 50, 4868, 70 mg, 0.19 mmol) and but-3-yn-1-ol (27 mg, 0.38 mmol) were dissolved in t-BuOH/H2O (1 mL: 0.5 mL), added with CuSO4 (7 mg, 0.042 mmol) and Sodium ascorbate (8 mg, 0.042 mmol), and agitated at a room temperature for 1 hour. The reacting solution was concentrated under vacuum, added with H2O (5 mL) and extracted with DCM (10 mL×2). Collected organic layer was washed with brine, dried with Na2SO4, filtrated and concentrated under vacuum. The concentrated product was purified with column chromatography ((MC:MeOH:H2O:NH4OH=280:20:1:1), to obtain the subject compound (86 mg).

Provenance & Evidence