Hydrogen Peroxide → HCID 13957778, compound

HRID 2308923Notes

Reaction equation

HRID 2308923 reaction equation
[F:1][CH:2]([F:24])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([CH:18]=[CH2:19])[C:4]=1[C:20]([O:22][CH3:23])=[O:21].OO.C(=O)(O)[O-:28].[Na+]>C(O)C>[F:24][CH:2]([F:1])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([CH:18]2[CH2:19][O:28]2)[C:4]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 13957750HCID 13957750, compound

Product 1

HCID 13957778HCID 13957778, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 14.0 g (0.039 mole) of product of Example 99, 105 ml of ethanol, 70 ml (0.60 mole) of 30% hydrogen peroxide, and 2.9 g (0.033 mole) of sodium bicarbonate is heated at 70° C. for 3 hours. The reaction mixture is cooled and concentrated in vacuo to approximately 30 ml then extracted with 75 ml of methylene chloride. The methylene chloride solution is washed with 300 ml of water. The aqueous layer is extracted twice with 75 ml of methylene chloride. The combined methylene chloride extracts were dried over magnesium sulfate and concentrated. The residue is purified by HPLC using 8% ethyl acetate/cyclohexane as eluent to give a yellow solid which after recrystallization from hexane/ether gave 2.32 g of the desired product as a white solid; m.p. 57.5°-59° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated in vacuo to approximately 30 ml
  3. extractionthen extracted with 75 ml of methylene chloride
  4. washThe methylene chloride solution is washed with 300 ml of water
  5. extractionThe aqueous layer is extracted twice with 75 ml of methylene chloride
  6. dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by HPLC
  9. customto give a yellow solid which
  10. customafter recrystallization from hexane/ether

Sources & evidence

ORD record
ord-4da66eca4fcc49f19c039c0dade47309
Source dataset
uspto-grants-1987_09
Patent number
US04692184

Reaction notes

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