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

HRID 747210노트

반응식

HRID 747210 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 76299Silver trifluoroacetate촉매HCID 22555007Acetonitrile chloroform용매

실험 절차

[(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.

후처리

  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

출처 및 근거

ORD 기록
ord-be68cb7fb38c48559f7522e153fb400c
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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