Carbamate → HCID 69983039, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.39 ml, 2.24 mmol) was added dropwise to a stirred solution at 5° C. under nitrogen of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one (3.48 g, 7.47 mmol) in dichloromethane (60 ml), followed by 1-chloroethyl chloroforrnate (1.05 ml, 9.73 mmol). The mixture was stirred at 5° C. for 2 hours and the intermediate carbamate was freed from benzyl chloride by flash-column chromatography (silica gel. Merck 7736), eluting with a gradient of 10-30% EtOAc in isohexane. The carbamate was heated in refluxing MeOH (40 ml) for 1 hour. Solvent was evaporated and the residue triturated with ether to give 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(3-fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one hydrochloride as a solid in 82% yield MS: 376 (MH+)(free base); NMR; 2.67 (2H, s); 3.3 (2H+DMSO); 3.75 (2H, s); 4.0 (1H, m); 4.25 (1H, t); 4.7 (2H, m); 5.14 (1H, m); 6.05 (1H, s); 7.4 (2H, m): 7.55 (1H, d); 8.42 (1H, s); 9.35 (1H, bs).

Provenance & Evidence