Carbamate → HCID 70022888, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (52 mg, 0.4 mmol) was added dropwise to a stirred solution at 5° C. under nitrogen of 5(R)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptan-5-yl]-3-fluorophenyl)oxazolidin-2-one (0.65 g, 1.35 mmol) in dichloromethane (10 ml), followed by 1-chloroethyl chlorofornate (0.19 ml, 1.76 mmol). The mixture was stirred at 5° C. for 2 hours and the interrnediate carbamate was freed from benzyl chloride by trituration with three portions of isohexane (3×15 ml). The carbarnate was heated in refluxing MeOH (10 ml) for 1 hour. Solvent was evaporated and the residue triturated with acetone to give the title product as a solid (0.366 g, 63% yield). MS: 391 (MH+); NMR(CDCl3); 2.0 (2H, dd); 3.2-3.34 (2H+DMSO); 3.56 (2H, dd); 3.9 (1H, m); 4.18 (1H, t); 4.34 (1H, s); 4.5 (1H, s); 5.07 (1H, m); 6.86 (1H, t); 7.15 (1H, d); 7.45 (1H, d); 8.42 (1H, s); 9.04 (1H, bs); 9.57 (1H, bs).

Provenance & Evidence