Hydrogen Peroxide → HCID 59840874, compound

HRID 1875714Notes

Reaction equation

HRID 1875714 reaction equation
C([C@@H]1COC(=O)N1[C:14]([C@@H:16]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:17][N:18]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:15])C1C=CC=CC=1.[Li+].[OH-].OO.[O-:42]S([O-])=O.[Na+].[Na+]>>[CH2:27]([O:26][N:18]([CH2:17][C@H:16]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:14]([OH:15])=[O:42])[C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 86659296HCID 86659296, compound

Product 1

HCID 59840874HCID 59840874, compound

Procedure

A solution of tert-butyl ((2S)-2-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-methylpentyl)(benzyloxy)carbamate (1.66 g, 3.25 mmol), LiOH (156 mg, 6.5 mmol, 2 eq.) and an aqueous solution of H2O2 (30%, 1.33 mL, 4 eq.), was stirred overnight. A saturated solution of Na2SO3 was added at 0° C. The mixture was extracted with a saturated solution of NaHCO3, washed with DCM (3×). The aqueous layer was saturated with NaCl, acidified up to pH 2 with an aqueous solution of HCl (5 N), then extracted with DCM (2×), EtOAc (2×), Et2O (2×). The combined organic layers were dried over MgSO4, filtered and evaporated to give 300 mg of the title product as a colorless oil used as such in the next step. M− (LC-MS (ESI)): 350.3.

Workup

  1. extractionThe mixture was extracted with a saturated solution of NaHCO3
  2. washwashed with DCM (3×)
  3. extractionextracted with DCM (2×), EtOAc (2×), Et2O (2×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c8c311cba4ee474fadc804056962923f
Source dataset
uspto-grants-2012_11
Patent number
US08309579B2

Reaction notes

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