m-Chloroperbenzoic acid → Lansoprazole

HRID 1901974Notes

Reaction equation

HRID 1901974 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].ClC1C=CC=C(C(OO)=[O:33])C=1.C(O)C.O>C(Cl)(Cl)Cl>[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:33])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 1094080Lansoprazole sulfideHCID 19096565Water ethanol

Product 1

HCID 3883LansoprazoleYield 74.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (monohydrate) (20 g) was dissolved in chloroform (200 ml), to which was added slowly dropwise below 5° C. a solution of m-chloroperbenzoic acid (13.5 g) in chloroform (200 ml), and stirred at the same temperature for about 10 minutes. After completion of the reaction, the reaction mixture was washed with a solution of sodium hydrogencarbonate, and dried over magnesium sulfate, and chloroform was evaporated off under reduced pressure. To the residue was added ethanol (100 ml) for crystallization, which was ice-cooled; the resulting crystals were collected by filtration and washed with ice-cooled ethanol. The crystals thus obtained were treated with a mixture of ethanol-water (9:1, 90 ml), heated (65°-70° 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 (14.9 g, yield: 74.9%).

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with a solution of sodium hydrogencarbonate
  3. dry with materialdried over magnesium sulfate, and chloroform
  4. customwas evaporated off under reduced pressure
  5. additionTo the residue was added ethanol (100 ml)
  6. customfor crystallization, which
  7. temperaturecooled
  8. filtrationthe resulting crystals were collected by filtration
  9. washwashed with ice-
  10. temperaturecooled ethanol
  11. customThe crystals thus obtained
  12. temperatureheated (65°-70° C.)
  13. stirringstirred so that the crystals
  14. dissolutionwere dissolved
  15. customthe insoluble matters were removed by hot filtration
  16. temperaturecooled for crystallization
  17. filtrationthe crystals were collected by filtration
  18. washwashed with ice-
  19. temperaturecooled ethanol-water mixture (8:2)
  20. customdried in vacuo

Sources & evidence

ORD record
ord-8764a5dcf2354940a7319f6651105347
Source dataset
uspto-grants-1996_11
Patent number
US05578732

Reaction notes

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