Hydrogen Peroxide → HCID 66845563, compound

HRID 715060Notes

Reaction equation

HRID 715060 reaction equation
[Li+].[OH-].OO.C([C@@H]1COC(=O)N1[C:18](=[O:45])[C@H:19]([C@H:31]1[N:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:34](C)(C)[CH2:33][CH2:32]1)[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[C:22]([F:30])[CH:21]=1)C1C=CC=CC=1.[O-:46]S([O-])=O.[Na+].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1.[Cl-].[Na+].O.O>[C:39]([O:38][C:36]([N:35]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:19]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[C:22]([F:30])[CH:21]=1)[C:18]([OH:45])=[O:46])=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516920Potassium bisulfateHCID 117965479HCID 117965479, compound

Product 1

HCID 66845563HCID 66845563, compoundYield 83.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of THF (100 mL), water (50 mL) and 1M LiOH (5.70 mL, 5.70 mmol) cooled to 0° C. was added H2O2 (0.728 mL, 7.13 mmol) and the mixture was agitated for 10 min. A solution of 52 (1.65 g, 2.85 mmol) in THF (20 mL) was added, and the mixture was allowed to warm to RT and agitate overnight. 1M Na2SO3 (20 mL) was added, and the mixture was agitated for 15 minutes. The mixture was acidified with 2M KHSO4, and brine (100 mL) was added. The aqueous phase was separated and extracted twice with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and evaporated. The crude product was purified by SiO2 chromatography (Flash 40L) eluting with 20% EtOAc/hexane containing 1% HOAc to afford 1.0 g (83.6%) of 57 as a solid.

Workup

  1. stirringagitate overnight
  2. stirringthe mixture was agitated for 15 minutes
  3. additionwas added
  4. customThe aqueous phase was separated
  5. extractionextracted twice with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by SiO2 chromatography (Flash 40L)
  11. washeluting with 20% EtOAc/hexane containing 1% HOAc

Sources & evidence

ORD record
ord-74ed14fbdea54d8e98837a52d9625176
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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