Hydrogen Peroxide → HCID 68181133, compound

HRID 2371298Notes

Reaction equation

HRID 2371298 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)[C:12](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:13])=[CH:6][CH:5]=1.[OH:40]O.[Li+].[OH-]>C1COCC1.O>[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@@H:11]([C:12]([OH:13])=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67487803HCID 67487803, compound

Product 1

HCID 68181133HCID 68181133, compoundYield 134.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of the (R)-diastereomer of 4-{3-(4-(R)-Benzyl-2-oxo-oxazolidin-3-yl)-2-[4-(3,3-dimethyl-but-1-enyl)-phenyl)-3-oxo-propyl}-benzoic acid methyl ester (0.43 g, 0.81 mmol) in THF/H2O (20 mL) (3:1) at room temperature were added H2O2 (2.2 mL, 8.1 mmol 35% in H2O) followed by LiOH (40 mg, 1.63 mmol). The reaction mixture was stirred for 3 h, at room temperature, quenched with (0.1 N HCl). The reaction mixture was extracted with ethyl acetate (100 mL) and dried over MgSO4, filtered and concentrated under reduced pressure to afford corresponding acid. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2/MeOH 2%-15% to afford the title compound (0.4 g, 100%).

Workup

  1. customquenched with (0.1 N HCl)
  2. extractionThe reaction mixture was extracted with ethyl acetate (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford corresponding acid
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH 2%-15%

Sources & evidence

ORD record
ord-f5f33fe1dcb4491c9f585fec7614ca5c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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