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

HRID 584910Notes

Reaction equation

HRID 584910 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a2bf0e80c487414194a9034d9f25f566
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…