HCID 11222326, compound → HCID 10173120, compound

Participants

Reaction Steps

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl)-oxazolidin-2-one (Reference Example 2) (0.7 g, 1.9 mmol) and (1-fluoroethenyl)-phenylsulfane dioxide (0.7 g, 3.8 mmol) (D. P. Mathews and J. R. McCarthy, JOC 55 (9), 1990, p 2973) were suspended/dissolved in toluene (5 ml) and heated to reflux under stirring for 2 days. The reaction mixture was cooled to room temperature, diluted with dichloromethane, washed with phosphate buffer (pH 7) and dried over sodium sulfate. Chromatography on silica gel with hexanes/acetone (1:1) gave 28 mg (4%) of the title compound as a colourless solid (Rf ˜0.25, TLC:hexanes/acetone, 1:1). The major product was the corresponding 5-fluoro-1,2,3-triazoyl compound with an Rf of ˜0.2.

Provenance & Evidence