Water → (5R)-3-[4-(3,6-Dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[(4-ethoxy-1H-1,2,3-triazol-1-yl)methyl]-2-oxazolidinone

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) (733 mg, 2.0 mmol) was dissolved in dry acetonitrile (8 ml). Ethoxyacetylene (420 mg, 6.0 mmol), 2,6-lutidine (236 mg, 2.2 mmol) and copper iodide (38 mg, 10 mmol %) were added and the resulting mixture was stirred at room temperature for 12 hours. Water was added and the mixture was extracted with dichloromethane (3×100 ml). The combined organic layers were concentrated under vacuum and the residue was purified by flash chromatography on silica gel with 5% of methanol in dichloromethane to give the title product (666 mg).

Provenance & Evidence