(S)-4-Benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-one → (S)-4-Benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

HRID 1268947Notes

Reaction equation

HRID 1268947 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:40])[C@@H:15]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[CH:20][CH:19]=1)[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:40])[C@@H:15]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[C@H:16]([OH:17])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69504531(S)-4-Benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69504636(S)-4-Benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-oneYield 111.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-4-benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-one (9.80 g) obtained from Reference example 20(b) in ethanol (150 ml) was added 5% palladium-charcoal (1.00 g), and the reaction solution was stirred at 50° C. for 4 hours in an atmosphere of hydrogen. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure. Water was added to the residue, and the resulting solution was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the target compound (9.10 g) was obtained as a foam.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resulting solution was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-c212ec27a0da44e898356890dac2d085
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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