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(S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]- acetamide

iodine monochloride

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title compound

(S)-N-[[3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide

용매

acetic acid

trifluoroacetic acid

ether

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후처리

1. 1
   기타the solids collected under reduced pressure through a medium-porosity sintered glass
2. 2
   여과filter
3. 3
   세척washing with ether
4. 4
   workup.DISSOLUTIONThe crude solids are dissolved in hot chloroform (a little methanol
5. 5
   workup.ADDITIONis added),
6. 6
   기타transferred to a separatory funnel
7. 7
   세척washed with saturated aqueous sodium bicarbonate, 20% aqueous sodium thiosulfate and brine
8. 8
   기타The organic phase is separated
9. 9
   건조dried over sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated under reduced pressure

실험 절차

(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).

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