Hydrogen Peroxide → HCID 57887016, compound

HRID 1819326Notes

Reaction equation

HRID 1819326 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].OO.[Cl:9][C:10]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:11]=1[CH2:12][N:13]1[C:21]2[C:20](=[O:22])[N:19]([CH3:23])[C:18]([C:24]#[N:25])=[N:17][C:16]=2[C:15]([C:26]#[N:27])=[C:14]1[N:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:29]1.S([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.O>[NH2:25][C:24]([C:18]1[N:19]([CH3:23])[C:20](=[O:22])[C:21]2[N:13]([CH2:12][C:11]3[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:10]=3[Cl:9])[C:14]([N:28]3[CH2:33][CH2:32][CH2:31][C@@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:40])[CH3:38])[CH2:29]3)=[C:15]([C:26]#[N:27])[C:16]=2[N:17]=1)=[O:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 86625682tert-Butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 57887016HCID 57887016, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (42 mg) and then an aqueous hydrogen peroxide solution (a 30-35% aqueous solution, 170 μl) were added dropwise to a solution of tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (162 mg) in a mixture of dimethyl sulfoxide (10 ml) and water (2 ml), and the resulting mixture was stirred overnight at room temperature. A 10% aqueous sodium sulfite solution was added to the reaction solution, followed by extraction with ethyl acetate (200 ml). The organic layer was washed with a 10% aqueous potassium carbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (77 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 ml)
  2. washThe organic layer was washed with a 10% aqueous potassium carbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b7c49624145e450d97786597f68a891d
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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