Trichloroisocyanuric Acid → (2-Oxo-1,3-oxazolidin-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-hydroxy-ethyl)-oxazolidin-2-one (0.575 g, 4.38 mmol) in acetone (40 ml) was added 15% aqueous sodium bicarbonate (12 ml) to give a white slurry, which was then cooled to 0° C. (JOC 2003, 68, 4999-5001). Sodium bromide (0.090 g, 0.88 mmol) and TEMPO (0.014 g, 0.09 mmol) were added and the resulting mixture was stirred for 10 minutes followed by the addition of trichloroisocyanuric acid (2.03 g, 8.76 mmol) in four equal portions added every five minutes. The pale yellow slurry was warmed to 25° C. and stirred for an additional 12 hours to yield a yellow solution. Iso-propanol (3 ml) was added and the mixture was stirred for 45 minutes to give a white slurry, which was filtered through a Celite® cake. The filtrate was concentrated in vacuo, quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The aqueous phase was acidified with 4N HCl until pH ˜2 and then put on for continuous extraction with methylene chloride (˜100 ml) for 16 hours. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to yield (2-oxo-oxazolidin-3-yl)-acetic acid (0.445 g, 70%) as a pale yellow solid.

Provenance & Evidence