Iodine chloride → (S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

HRID 583568

反応式

HRID 583568 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:6][CH:7]=1.[I:19]Cl>C(O)(=O)C.FC(F)(F)C(O)=O.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:19]

参加物

6

反応物 2

HCID 24640Iodine chlorideHCID 11345751(S)-N-[[3-(3-Fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide

生成物 1

HCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-f725227dec0845f084ddacb0005cc789
出典データセット
uspto-grants-1999_07
特許番号
US05929248

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