Sodium Sulfite → HCID 23077745, compound

HRID 1349463Notes

Reaction equation

HRID 1349463 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:35])[CH:11]=[C:12]([CH:29]([OH:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:35])[CH:11]=[C:12]([C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 23077499HCID 23077499, compound

Product 1

HCID 23077745HCID 23077745, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the above-mentioned crude 9-benzyloxy-2-(3,4-dichlorobenzyl)-6-(1-hydroxy-2,2-dimethylpropyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (132 mg) in chloroform (4 ml) was added Dess-Martin reagent (65 mg) and the mixture was stirred at room temperature for 20 min. Saturated aqueous sodium hydrogen carbonate solution and sodium sulfite were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (ethyl acetate:chloroform=4:1) to give 9-benzyloxy-2-(3,4-dichlorobenzyl)-6-(2,2-dimethylpropionyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (38 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:chloroform=4:1)

Sources & evidence

ORD record
ord-0b4a32e21b2549a69bb43d24144e24c7
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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