Hydrogen Peroxide → (S)-2-methyl-5-phenylpentanoic acid

HRID 59695Notes

Reaction equation

HRID 59695 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:26])[C@@H:15]([CH3:25])[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1.OO.[OH-].[Li+].[OH:31]S([O-])(=O)=O.[K+]>>[CH3:25][C@@H:15]([CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:14]([OH:26])=[O:31]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 90054465(S)-4-benzyl-3-((S)-2-methyl-5-phenylpentanoyl)oxazolidin-2-one

Product 1

HCID 90054467(S)-2-methyl-5-phenylpentanoic acidYield 95%

Procedure

To a stirring aqueous mixture cooled to 0° C. comprising (S)-4-benzyl-3-((S)-2-methyl-5-phenylpentanoyl)oxazolidin-2-one (21mb(i), 563 mg, 1.60 mmol) was added hydrogen peroxide and lithium hydroxide. The resulting reaction mixture was stirred for four hours. The reaction mixture was acidified with 5% KHSO4 and extracted twice with ethyl acetate, the organic layer was washed twice with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel chromatography. Elution with ethyl acetate-heptane-acetic acid (25:75:0.4) afforded the title compound (293 mg, 95%) as a colorless oil; TLC Rf 0.35 (solvent system: 25:75:0.4 v/v/v ethyl acetate-heptane-acetic acid); HPLC retention time 12.08 min, stationary phase: Chiralpak IA 4.6×25 mm 5μ, ultraviolet detector at 210 nm, mobile phase: 1 mL/min 99:1:0.1 heptane: 2-propanol:acetic acid, 97.22% (S), 2.78% (R).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted twice with ethyl acetate
  3. washthe organic layer was washed twice with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography
  7. washElution with ethyl acetate-heptane-acetic acid (25:75:0.4)

Sources & evidence

ORD record
ord-f86baa8d3d574753b944dfa32129d500
Source dataset
uspto-grants-2016_09
Patent number
US09440919B2

Reaction notes

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