Sodium Thiosulfate → HCID 22248470, compound

HRID 890121Notes

Reaction equation

HRID 890121 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][S:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[C:14](=[O:19])[NH:15][CH:16]=[CH:17][N:18]=2)[CH2:8][CH2:7]1.ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][S:5]([CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[C:14](=[O:19])[NH:15][CH:16]=[CH:17][N:18]=2)[CH2:10][CH2:11]1)=[O:32]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 222485193-(4-(2-fluorobenzylthio)piperidino]methyl-1H-pyrazin-2-one

Product 1

HCID 22248470HCID 22248470, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After dissolving 57 mg of 3-[4-(2-fluorobenzylthio)piperidino]methyl-1H-pyrazin-2-one in 3 ml of dichloromethane, 31 mg of 3-chloroperbenzoic acid was added at below −70° C., the mixture was stirred for 30 minutes, and then an additional 5 mg of 3-chloroperbenzoic acid was added and the stirring was continued for 20 minutes. Aqueous sodium thiosulfate solution was added to the reaction solution and extraction was performed with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform/methanol/ammonia water) to obtain the title compound (16 mg, 27% yield).

Workup

  1. additionwas added at below −70° C.
  2. waitthe stirring was continued for 20 minutes
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (solvent: chloroform/methanol/ammonia water)

Sources & evidence

ORD record
ord-036262af1fa74d0ebecbbbe582173373
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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