Hydrogen Peroxide → HCID 59840874, compound

HRID 1672167Notes

Reaction equation

HRID 1672167 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:16][C@@H:17]([C:22](N1[C@H](CC2C=CC=CC=2)COC1=O)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].OO.[O-:42]S([O-])=O.[Na+].[Na+]>>[CH2:9]([O:8][N:7]([CH2:16][C@H:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:22]([OH:23])=[O:42])[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:37])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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-3b56e395b0d348319c6c62835b4a425e
Source dataset
uspto-grants-2011_08
Patent number
US07998964B2

Reaction notes

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