Hydrogen Peroxide → Lansoprazole

HRID 1901970Notes

Reaction equation

HRID 1901970 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].OO.S([O-])([O-])(=[O:29])=S.[Na+].[Na+].C(O)C.O>ClCCl.C(O)(C)(C)C.[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5]>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:29])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 1094080Lansoprazole sulfideHCID 19096565Water ethanol

Product 1

HCID 3883LansoprazoleYield 140.4%

Reagents, catalysts & solvents 3

HCID 178419084HCID 178419084, compoundCatalystHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (monohydrate) (1.77 g) was dissolved in dichloromethane (30 ml), to which was added dropwise at 15°-20° C. a solution of hydrogen peroxide in t-butanol (2.75 ml corresponding to 0.2 g of hydrogen peroxide) containing vanadium pentaoxide (5 mg), and then allowed to react at 20°-25° C. for about one hour. After completion of the reaction, an aqueous solution of sodium thiosulfate (0.5 g/30 ml) was added to the reaction mixture, which was stirred vigorously for about 10 minutes, allowed to stand still, and separated into layers. The dichloromethane layer was washed with water (30 ml), and concentrated under reduced pressure; to the residue was added a mixture of ethanol-water (9:1, 10 ml) for crystallization. This solution was ice-cooled, and the crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water (8:2). The crystals thus obtained were treated with a mixture of ethanol-water (9:1, 10 ml), heated (65°-70° C.) and stirred for dissolution of the crystals, then the insoluble matters were removed by hot filtration. The filtrate was ice-cooled for crystallization, and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture (8:2) and dried in vacuo to give white crystals of 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylsulfinyl]benzimidazole (1.64 g). (yield: 93.2%).

Workup

  1. customto react at 20°-25° C. for about one hour
  2. customAfter completion of the reaction
  3. customseparated into layers
  4. washThe dichloromethane layer was washed with water (30 ml)
  5. concentrationconcentrated under reduced pressure
  6. additionto the residue was added
  7. additiona mixture of ethanol-water (9:1, 10 ml)
  8. customfor crystallization
  9. temperaturecooled
  10. filtrationthe crystals were collected by filtration
  11. washwashed with an ice-
  12. temperaturecooled
  13. additionmixture of ethanol-water (8:2)
  14. customThe crystals thus obtained
  15. temperatureheated (65°-70° C.)
  16. stirringstirred for dissolution of the crystals
  17. customthe insoluble matters were removed by hot filtration
  18. temperaturecooled for crystallization
  19. filtrationthe crystals were collected by filtration
  20. washwashed with ice-
  21. temperaturecooled ethanol-water mixture (8:2)
  22. customdried in vacuo

Sources & evidence

ORD record
ord-5d0f7acfcc8a42bf829315cc58648de9
Source dataset
uspto-grants-1996_11
Patent number
US05578732

Reaction notes

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