Hydrogen Peroxide → (2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

HRID 725640Notes

Reaction equation

HRID 725640 reaction equation
OO.C([C@@H]1COC(=O)N1[C:16](=[O:36])[C@H:17]([CH:33]([CH3:35])[CH3:34])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=1)C1C=CC=CC=1.[OH-].[Li+].S([O-])([O-])=[O:40].[Na+].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O>[CH:33]([C@@H:17]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=1)[C:16]([OH:36])=[O:40])([CH3:34])[CH3:35]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 22865791(R)-4-Benzyl-3-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)oxazolidin-2-one

Product 1

HCID 9944529(2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

Reagents, catalysts & solvents 1

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

Procedure

0.434 liter of 30% hydrogen peroxide is slowly added to 300 g of 4(R)-benzyl-3-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propionyl}-oxazolidin-2-one in 4.8 liters of tetrahydrofuran/water (3:1) at 0° C. After the addition of 31.2 g of lithium hydroxide, the mixture is stirred for 3 hours at 0°-20° C. 2.55 liters of 1.5M sodium sulfite solution are then added to the reaction mixture at 0°-15° C. and stirring is continued for a further 30 minutes. 1 liter of saturated sodium hydrogen carbonate solution is added and the tetrahydrofuran is evaporated off. The aqueous solution is washed repeatedly with dichloromethane and then acidified with 2N hydrochloric acid (pH 3.0). Extraction with dichloromethane and subsequent evaporation of the solvent yield the title compound: Rf (ethyl acetate/hexane=2:1)=0.30; m.p. 43.5°-44° C.

Workup

  1. stirringstirring
  2. waitis continued for a further 30 minutes
  3. customthe tetrahydrofuran is evaporated off
  4. washThe aqueous solution is washed repeatedly with dichloromethane
  5. extractionExtraction
  6. customwith dichloromethane and subsequent evaporation of the solvent

Sources & evidence

ORD record
ord-80caa10ef6ca438ba009362d030fa53d
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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