Methanesulfonyl chloride → 5(R)-Imidazol-2-ylthiomethyl-3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one

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Reaction Conditions

Reaction Steps

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.1 ml, 0.674 mmol) was added to a stirred suspension of 5(R)-methanesulfonyloxymethyl 3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one (prepared from the 5(R)-hydroxymethyl compound (WO97/09328) by reaction with methylsulfonyl chloride) (0.25 g, 0.674 mmol) and 2-mercaptoimidazole (0.067 g, 0.674 mmol) in dioxan (2 ml) under nitrogen. The mixture was heated at 60° C. for 4 hours and evaporated. The residue was purified by column chromatography, eluting first with 2% MeOH/EtOAc and then with 4% MeOH/EtOAc to give the title product as a solid (0.077 g, 30%); mp 178-179° C. (dec.) MS: 476 (MH+); NMR: 2.39 (2H, bs); 3.42 (2H, m); 3.79 (2H, t); 3.86 (1H, m); 4.19 (3H, m); 4.89 (1H, m); 6.07 (1H, s); 7.04 (2H, s); 7.26 (1H, dd); 7.38 (1H, t); 7.46 (1H, d).

Provenance & Evidence