Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isothiazol-3-yloxymethyl)oxazolidin-2-one

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Reaction Steps

Diisopropylazodicarboxylate (227 mg, 1.12 mmol) was added dropwise, at ambient temperature, to a stirred solution of 5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (300 mg, 1.02 mmol ; see Example 1), 3-hydroxyisothiazole (114 mg, 1.13 mmol) and triphenylphosphine (304 mg, 1.16 mmol) in THF (8.0 ml). The resulting solution was stirred at room temperature for 30 minutes before evaporating the solvent to give an orange oil. It was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (3:2)) to give the title product (257 mg, 67%) as a colourless crystalline solid. MS: ESP+ (M+H)+=377.

Provenance & Evidence