Hydrogen Peroxide → N-{4'-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

HRID 584909Notes

Reaction equation

HRID 584909 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][O:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.C(BCCCC)CCC.[CH:37]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]([CH3:61])[C:53](=[O:60])[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]=2)=[CH:41][CH:40]=1)=[O:38].OO>ClCCl.CO.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@@H:15]([O:16][CH2:17][CH3:18])[C@@H:37]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]([CH3:61])[C:53](=[O:60])[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[CH:46]=2)=[CH:41][CH:40]=1)[OH:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamideHCID 178440534HCID 178440534, compound

Product 1

HCID 69693998N-{4'-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamideYield 48%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.8 g (6.7 mmol) of (S)-4-benzyl-3-(2-ethoxy-ethanoyl) oxazolidin-2-one amd 15 ml of dichloromethane are introduced into a three-necked flask under argon. 7.3 ml (8 mmol) of dibutylborane trifluoromethane-sulfonate and 1.3 ml (8 mmol) of diisopropylethylamineare successively added dropwise at 0° C., and the mixture is stirred for one hour. At −78° C., a solution of 2 g (6 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared in Example 1(e)) in 25 ml of dichloromethane is added and the mixture is stirred for one hour. The mixture is allowed to warm to 0° C. and is treated with a pH 7 buffer solution (16 ml) in 45 ml of methanol and then with aqueous hydrogen peroxide solution (16 ml) in 45 ml of methanol and stirred for one hour at 0° C. The reaction medium is poured into water and extracted with dichloromethane, 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 (60/40). 1.7 g (48%) of N-{4′-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide are obtained.

Workup

  1. stirringthe mixture is stirred for one hour
  2. extractionextracted with dichloromethane
  3. customthe organic phase is separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (60/40)

Sources & evidence

ORD record
ord-1f721bcc9e064ad2b69ad87fe0b2dff0
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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