Hydrogen Peroxide → Lansoprazole

HRID 1901972Notes

Reaction equation

HRID 1901972 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>C(O)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

7

Reactant 4

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

Product 1

HCID 3883LansoprazoleYield 381%

Reagents, catalysts & solvents 2

HCID 178419084HCID 178419084, compoundCatalystHCID 702EthanolSolvent2×

Procedure

2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (monohydrate) (20.0 g) was dissolved in ethanol (150 ml), to which was added dropwise at about 20° C. a solution of vanadium pentaoxide (30 mg) in a mixture of 35% aqueous solution of hydrogen peroxide (6.14 g) and ethanol (6 ml), and allowed to react at 18°-22° for about 2.5 hours. After completion of the reaction an aqueous solution of sodium thiosulfate (2 g/60 ml) was added to the reaction mixture, which was stirred by ice-cooling for about 1 hour. The crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water (1:1). The crystals thus obtained were treated with a mixture of ethanol-water (9:1, 100 ml), heated (70°-80° C.) and stirred so that the crystals were dissolved, 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 needles of 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylsulfinyl]benzimidazole (17.8 g). (yield: 89.5%).

Workup

  1. customto react at 18°-22° for about 2.5 hours
  2. additionwas added to the reaction mixture, which
  3. temperaturecooling for about 1 hour
  4. filtrationThe crystals were collected by filtration
  5. washwashed with an ice-
  6. temperaturecooled
  7. additionmixture of ethanol-water (1:1)
  8. customThe crystals thus obtained
  9. temperatureheated (70°-80° C.)
  10. stirringstirred so that the crystals
  11. dissolutionwere dissolved
  12. customthe insoluble matters were removed by hot filtration
  13. temperaturecooled for crystallization
  14. filtrationthe crystals were collected by filtration
  15. washwashed with ice-
  16. temperaturecooled ethanol-water mixture (8:2)
  17. customdried in vacuo

Sources & evidence

ORD record
ord-d84b4293ccb4438b9ece6d4dd8bc2d5f
Source dataset
uspto-grants-1996_11
Patent number
US05578732

Reaction notes

Loading…