Dichloromethane → N-{4'-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

HRID 584910ノート

反応式

HRID 584910 の反応式
B(F)(F)F.CCOCC.ClCCl.C[SiH](C)C.[CH2:17]([C@H:24]1[CH2:28][O:27][C:26](=[O:29])[N:25]1[C:30](=[O:60])[C@@H:31]([O:57][CH2:58][CH3:59])[C@@H:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]([CH3:56])[C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:41]=2)=[CH:36][CH:35]=1)O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([C@H:24]1[CH2:28][O:27][C:26](=[O:29])[N:25]1[C:30](=[O:60])[C@@H:31]([O:57][CH2:58][CH3:59])[CH2:32][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]([CH3:56])[C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:41]=2)=[CH:36][CH:35]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 70435TrimethylsilaneHCID 69693998N-{4'-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

生成物 1

HCID 69694199N-{4'-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

320 μl (2.6 mmol) of boron trifluoride etherate and 5 ml of dichloromethane are introduced into a three-necked flask under a stream of nitrogen. At 0° C., 800 μl (5 mmol) of trimethylsilyl hydride are added dropwise, followed by portionwise addition of 380 mg (0.64 mmol) of N-{4′-[(1R,2S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide. After one hour at room temperature, the mixture is heated at 50° C. for 20 hours. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). 280 mg (76%) of the expected product are obtained.

後処理

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (70/30)

出典と根拠

ORDレコード
ord-a2bf0e80c487414194a9034d9f25f566
出典データセット
uspto-grants-2005_08
特許番号
US06927228B2

反応ノート

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