Methanol → (5R)-3-[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one

Participants

Reaction Steps

(5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one (Intermediate 48) (1.10 g, 3.39 mmol), 5-methyl-2H-tetrazole (0.347 g, 4.09 mmol), polystyrene-triphenylphosphine (phosphine loading 1.51 mmol/g, 3.79 g, 5.72 mmol) and diisopropyl azodicarboxylate (0.856 g, 4.11 mmol) were reacted as described for Example 29 to afford the title product (0.632 g) after chromatography on silica gel with 5% methanol in dichloromethane. The regioisomeric product (5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-[(5-methyl-1H-tetrazol-1-yl)methyl]-1,3-oxazolidin-2-one was also isolated (0.369 g).

Provenance & Evidence