Hydrogen Peroxide → HCID 53730440, compound

HRID 400236Notes

Reaction equation

HRID 400236 reaction equation
[O:1]=[C:2](N1[C@@H](CC2C=CC=CC=2)COC1=O)[C@@H:3]([C:14](=O)[CH2:15]C(C)(C)C)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.OO.[OH2:36].[OH-:37].[Li+].S([O-])([O-])=O.[Na+].[Na+].[OH-:45].[Na+]>C1COCC1.O.O>[CH3:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][CH:3]([CH2:14][C:15]([O:45][C:3]([CH3:14])([CH3:4])[CH3:2])=[O:37])[C:2]([OH:1])=[O:36])=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 22851172HCID 22851172, compound

Product 1

HCID 53730440HCID 53730440, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of the oxazolidinone (2) (0.57 g, 1.23 mmol) in THF/water (4:1, 25 ml) was cooled in an ice bath and treated with hydrogen peroxide solution (27.5 wt. %, 4.9 mmol, 0.56 ml, 4 eq). The mixture was stirred for a few min. then treated dropwise with a solution of lithium hydroxide monohydrate (1.23 mmol, 52 mg, 1.0 eq) in water (5 ml). The reaction was stirred for 1.5 hr then treated with a 10% aqueous solution of sodium sulphite (5 ml). The reaction mixture was adjusted to pH 12-13 with 1M NaOH and then partitioned between dichloromethane and water. The aqueous layer was separated and acidified with 10% HCl. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed once with brine, once with NaHCO3 solution, dried (MgSO4) and the solvent removed to give the title compound (3) (0.18 g) as a yellowish oil which was used without further purification. δH (CDCl3) 1.43 (9H, s), 1.51-1.79 (4H, m), 2.32 (3H, s), 2.37 (1H, dd), 2.92 (1H, m), and 7.03-7.12 (4H, m).

Workup

  1. stirringThe reaction was stirred for 1.5 hr
  2. custompartitioned between dichloromethane and water
  3. customThe aqueous layer was separated
  4. extractionThe aqueous layer was extracted three times with EtOAc
  5. washThe combined organic layer was washed once with brine, once with NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed

Sources & evidence

ORD record
ord-2f6a010ebf42470285514ee185c31f15
Source dataset
uspto-grants-1998_10
Patent number
US05827890

Reaction notes

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