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Acetic Acid → Pantoprazole

HRID 492140
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 492140
[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.C([O-])([O-])=[O:27].[Na+].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].C(O)(=O)C>CO.O.OO>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S+:11]([O-:27])[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 9799341Pantoprazole sulfide

Produkt 1

HCID 178493214PantoprazoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 784
Hydrogen Peroxide
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

2 g of 5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole was suspended in 36 ml of methanol at room temperature, to which 4.1 g of Na2CO3 in 14 ml water was added while stirring. 0.09 g of Na2WO4·2H2O oxidation catalyst was dissolved in 0.74 g H2O2 (50% aqueous solution), and further diluted with 10 ml of water. The oxidant/catalyst solution was added to the reactant/base solution dropwise so that the addition was completed in about 30 minutes while stirring at room temperature. The reaction was continued for additional 10 minutes-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. Finally, a precipitate was formed after adding a diluted acetic acid aqueous solution to a pH value of about 8, which was filtered, water washed, and dried in vacuo to obtain Pantoprazole with a yield of about 85% (LC purity>95%).

Aufarbeitung

  1. additionwas added
  2. additionThe oxidant/catalyst solution was added to the reactant/base solution dropwise so that the addition
  3. stirringwhile stirring at room temperature
  4. waitThe reaction was continued for additional 10 minutes
  5. stirring-while stirring
  6. customto remove methanol
  7. customFinally, a precipitate was formed
  8. filtrationwas filtered
  9. washwater washed
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-91e8e802388d49edbd31954606e58495
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07531666B2

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