Hydrogen Peroxide → 2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid

HRID 1060746Notes

Reaction equation

HRID 1060746 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:9](N2C(C(C)C)COC2=O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].OO.N([O-])=[O:35].[Na+]>C1COCC1>[CH:1]1([CH2:7][CH:8]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:9]([OH:10])=[O:35])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 186286692-Cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-ylbutane-1,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 218998342-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acidYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-yl-butane-1,4-dione (1.63 g, 4.13 mmol) in THF (20 mL) was treated with lithium hydroxide monohydrate (0.226 g, 5.37 mmol) and hydrogen peroxide (2 mL of a 30% solution) and the mixture was stirred overnight at ambient temperature. The mixture was treated with sodium nitrite (1.3 g) and stirred for an additional 30 minutes. The organic solvent was removed under reduced pressure and the residual mixture was diluted with water (30 mL). The dilution was extracted with methylene chloride (3×30 mL) and the aqueous layer was acidified to pH 2 with 1M hydrochloric acid and extracted with dichloromethane (3×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to dryness to provide 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid (0.56 g, 48%).

Workup

  1. stirringstirred for an additional 30 minutes
  2. customThe organic solvent was removed under reduced pressure
  3. additionthe residual mixture was diluted with water (30 mL)
  4. extractionThe dilution was extracted with methylene chloride (3×30 mL)
  5. extractionextracted with dichloromethane (3×20 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4d1c535ebe044a4b9b77efab639365e4
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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