Sodium Thiosulfate → Pantoprazole

HRID 492144Notes

Reaction equation

HRID 492144 reaction equation
[F:1][CH:2]([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][N:14]=3)=[N:10][C:6]=2[CH:5]=1.[O-:26]S([O-])(=S)=O.[Na+].[Na+]>CO.OO.O>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S+:11]([O-:26])[C:9]2[NH:8][C:7]3[CH:23]=[CH:24][C:4]([O:3][CH:2]([F:1])[F:25])=[CH:5][C:6]=3[N:10]=2)[C:18]=1[O:19][CH3:20]

Participants

6

Reactant 2

HCID 24477Sodium ThiosulfateHCID 9799341Pantoprazole sulfide

Product 1

HCID 178493214Pantoprazole

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.4 g of 5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole was suspended in 6 ml of methanol at room temperature. 0.02 g of Na2WO4·2H2O oxidation catalyst was dissolved in 0.109 g H2O2 (35% aqueous solution), and further diluted with 2 ml of water. The oxidant/catalyst solution was added to the reactant solution dropwise so that the addition was completed in about 30 minutes while stirring at room temperature. The reaction was continued for additional 5.5 hours while stirring. 10 ml of 10% Na2S2O3 aqueous solution was then added, and the resulting mixture was subjected to a reduced pressure to remove methanol therefrom, followed by adding a diluted acetic acid aqueous solution to a pH value of about 8. The resulting pH=8 mixture was extracted with ethyl acetate to obtain a crude product of Pantoprazole with a LC purity of about 52.5%.

Workup

  1. additionThe oxidant/catalyst solution was added to the reactant solution dropwise so that the addition
  2. waitThe reaction was continued for additional 5.5 hours
  3. stirringwhile stirring
  4. customto remove methanol
  5. additionby adding a diluted acetic acid aqueous solution to a pH value of about 8
  6. extractionThe resulting pH=8 mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-4c672c331c9f411f985e1976b1946b86
Source dataset
uspto-grants-2009_05
Patent number
US07531666B2

Reaction notes

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