Iodine → [(5R)-3-(4-Iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate

HRID 747210ノート

反応式

HRID 747210 の反応式
[CH3:1][S:2]([O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)(=[O:4])=[O:3].[I:19]I>C(Cl)(Cl)Cl.C(#N)C.FC(F)(F)C([O-])=O.[Ag+]>[CH3:1][S:2]([O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[CH2:8]1)(=[O:3])=[O:4]

参加物

5

反応物 2

HCID 807IodineHCID 15034707[(5r)-3-Phenyl-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate

生成物 1

HCID 24744103[(5R)-3-(4-Iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate収率 53%

試薬・触媒・溶媒 2

HCID 76299Silver trifluoroacetate触媒HCID 22555007Acetonitrile chloroform溶媒

実験手順

[(5R)-3-phenyl-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (41 g, 152 mmol) was dissolved in chloroform/acetonitrile (250/250 ml). Silver trifluoroacetate (50 g, 228 mmol) was added followed by portionwise addition of iodine (58 g, 228 mmol). After stirring the reaction overnight, the silver iodide was filtered off, and the filtrate was washed with solutions of 5% sodium thiosulfate (2×500 ml), saturated sodium bicarbonate (500 ml), brine, and dried over magnesium sulfate. The dried solution was evaorated to give the desired product as a yellow solid (32 g) that was used without further purification.

後処理

  1. customthe reaction overnight
  2. filtrationthe silver iodide was filtered off
  3. washthe filtrate was washed with solutions of 5% sodium thiosulfate (2×500 ml), saturated sodium bicarbonate (500 ml), brine
  4. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-be68cb7fb38c48559f7522e153fb400c
出典データセット
uspto-grants-2008_07
特許番号
US07396847B2

反応ノート

読み込み中…