Tert-Butyl hypochlorite → N-((3-Chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-N,N-dimethylpropan-1-aminium chloride

Participants

Reaction Steps

To a solution of N,N-dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)propan-1-aminium chloride (6.51 mmol) in MeOH (5 ml) was added, dropwise, tert-butylhypochlorite (˜2.5 ml) until the reaction mixture was clear with white precipitate. The solution was filtered through a 0.45 μm nylon filter, then evaporated and purified on preparative HPLC (H2O/MeOH) to afford the title compound as a white foam (248.1 mg, 0.9648 mmol, 15% over two steps). 1H NMR (D2O, 400 MHz) δ 0.99 (t, J=7.2 Hz, 3H), 1.64 (s, 3H), 1.8-2.0 (m, 2H), 3.24 (s, 3H), 3.26 (s, 3H), 3.40-3.45 (m, 2H), 3.75 (d, J=15.2 Hz, 1H), 3.82 (d, J=15.2 Hz, 1H), 4.62 (d, J=9.6 Hz, 1H), 4.90 (d, J=9.6 Hz, 1H). ESI/APCI expected for C10H20ClN2O2+: 235.12. Found: 235.

Provenance & Evidence