反应详情

(S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]- acetamide (PREPARATION 17, 0.280 g, 1.11 mmol) is dissolved in a mixture of acetic acid (20 ml) and trifluoroacetic acid (5 ml) and then treated with iodine monochloride (2.343 g, 14.43 mmol) at 20-25°. The mixture is stirred at 20-25° under nitrogen. After about 24 hr the reaction mixture is diluted with ether and the solids collected under reduced pressure through a medium-porosity sintered glass filter, washing with ether. The crude solids are dissolved in hot chloroform (a little methanol is added), transferred to a separatory funnel, and washed with saturated aqueous sodium bicarbonate, 20% aqueous sodium thiosulfate and brine. The organic phase is separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, mp 185.5-186.5°; [α]25D -37.6° (c 1.0, DMF).

1. customthe solids collected under reduced pressure through a medium-porosity sintered glass
2. filtrationfilter
3. washwashing with ether
4. dissolutionThe crude solids are dissolved in hot chloroform (a little methanol
5. additionis added),
6. customtransferred to a separatory funnel
7. washwashed with saturated aqueous sodium bicarbonate, 20% aqueous sodium thiosulfate and brine
8. customThe organic phase is separated
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure