Hydrogen Peroxide → 2-[8-(2-Methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyric acid

HRID 252414Notes

Reaction equation

HRID 252414 reaction equation
OO.O.[OH-].[Li+].C([C@@H]1COC(=O)N1C(=O)[CH:20]([CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[C:28]([O:35][CH2:36][CH2:37][O:38][CH3:39])[CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH:21]([CH3:23])[CH3:22])C1C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+].[C:47](=O)([O-:49])[OH:48].[Na+]>O1CCCC1.O>[CH3:39][O:38][CH2:37][CH2:36][O:35][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:27]=1[CH:26]=[C:25]([CH2:24][CH:20]([CH:21]([CH3:23])[CH3:22])[C:47]([OH:49])=[O:48])[CH:34]=[CH:33]2

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 668877734(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one

Product 1

HCID 668879102-[8-(2-Methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

122 ml of hydrogen peroxide (30%) are added dropwise and then 0.17 g of lithium hydroxide monohydrate is added to the solution of 0.95 g of 4(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one in 12 ml of tetrahydrofuran and 4 ml of water at 0° C. After 6 hours at room temperature, the reaction mixture is cooled to 0° C. and admixed with a solution of 1.54 g of sodium sulphite in 9 ml of water (negative peroxide test). The reaction mixture is adjusted to pH 9.8 with saturated aqueous sodium hydrogen-carbonate solution and clarified by filtration, and the tetrahydrofuran is concentrated by evaporation. The residue is washed with dichloromethane (3×)—the combined organic phases are washed with phosphate buffer/25% conc. ammonia solution (pH 9.8). The combined aqueous phases are adjusted to pH 3.0 with 4N HCl and extracted with dichloromethane (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

Workup

  1. filtrationclarified by filtration
  2. concentrationthe tetrahydrofuran is concentrated by evaporation
  3. washThe residue is washed with dichloromethane (3×)—the combined organic phases
  4. washare washed with phosphate buffer/25% conc. ammonia solution (pH 9.8)
  5. extractionextracted with dichloromethane (2×)
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5b430438d6bb4f8983b1df2d2a034ac5
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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