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

Participants

Reaction Steps

To a solution of N,N-dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)ethanaminium chloride (6.76 mmol) in MeOH (10 ml) was added, dropwise, tert-butylhypochlorite (1.6 ml, 10 mmol). The solution was stirred for 2 h, evaporated, and purified by preparative HPLC (H2O/MeOH) to afford the title compound as a white foam (667 mg, 2.59 mmol, 38% over two steps). 1H NMR (D2O, 400 MHz) δ 1.44 (t, J=7.2 Hz, 3H), 1.65 (s, 3H), 3.22 (s, 3H), 3.25 (s, 3H), 3.57 (q, J=7.2 Hz, 2H), 3.76-3.80 (m, 2H), 4.61 (d, J=9.6 Hz, 1H), 4.90 (d, J=9.6 Hz, 1H). ESI/APCI expected for C9H18ClN2O2+: 221.11. Found: 221.

Provenance & Evidence