Hydrogen Peroxide → HCID 10115004, compound

HRID 1830822Notes

Reaction equation

HRID 1830822 reaction equation
[NH2:1][C:2]1[C:28]([CH3:29])=[C:27]([CH3:30])[C:5]([O:6][CH2:7][C:8]([N:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])=[C:4]([CH3:31])[C:3]=1[CH3:32].OO.[OH-].[Na+].C(=O)([O-])[OH:38].[Na+]>CO>[NH2:1][C:2]1[C:3]([CH3:32])=[C:4]([CH3:31])[C:5]([O:6][CH2:7][C:8]([N:10]([CH3:11])[CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]([NH2:26])=[O:38])=[CH:23][CH:24]=3)[CH2:16][CH2:17]2)=[O:9])=[C:27]([CH3:30])[C:28]=1[CH3:29]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10203266HCID 10203266, compound

Product 1

HCID 10115004HCID 10115004, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture solution of 82 mg of the compound (18) obtained in the Example 18 in methanol were added 58 μl of 30% hydrogen peroxide aqueous solution and 150 μl of 3N-sodium hydroxide aqueous solution under ice-cooling, and the reaction mixture was stirred for 6 hours at the room the temperature. After the reaction, saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and extracted with dichloromethane. The organic layer was washed with saturated saline, dried and the solvent was removed under reduced pressure. The resulting residue was purified by amine coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : methanol =10:1) to give 66 mg (77%) of the above-mentioned compound (19).

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated saline
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by amine coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : methanol =10:1)

Sources & evidence

ORD record
ord-d336e762cf364347885445a5b34cdafc
Source dataset
uspto-grants-2006_06
Patent number
US07067533B2

Reaction notes

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