Pyridine → HCID 69982285, compound

Participants

Reaction Steps

A solution of (R)-2,2-dimethyl-1,3-dioxolan-4-ylcarbonyl chloride (S Handa et al, Synth. Commun. (1995), 25, 2837) [0.597 g, 3.63 mmol ] in dichloromethane (5 ml) was added dropwise to a stirred mixture of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(3-fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one hydrochloride (1 g, 2.42 mmol) and pyridine (0.49 ml, 6.06 mmol) in dichloromethane (30 ml) under nitrogen at −10° C. After 10 minutes the cooling bath was removed and the mixture stirred for a further hour. Water (30 ml) was added and the organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with ether and filtered to give 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(4-(1-(2,2-dimethyl-1,3-dioxolan-4(R)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one as a solid (1.13 g, 93%) MS: 504 (MH+); NMR: 1.32 (6H, s); 2.42 (2H+DMSO); 3.7 (2H, m); 4.0 (1H, m); 4.11 (2H, m); 4.25 (2H, m); 4.8 (2H, m); 4.91 (1H, m); 5.12 (1H, m); 6.02 (1H, s); 7.29-7.43 (2H, m); 7.5 (1H, d); 8.42 (1H, s).

Provenance & Evidence