Sodium Hydroxide → Lansoprazole

HRID 2116761Notes

Reaction equation

HRID 2116761 reaction equation
[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)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[OH-].[Na+].Cl[O-].[Na+].Cl[O-].S(S([O-])=O)([O-])(=O)=[O:33].[Na+].[Na+]>C(O)(=O)C.CC(C)=O.O.C(#N)C>[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)=[O:33])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 61739HypochloriteHCID 656671Sodium PyrosulfiteHCID 1094080Lansoprazole sulfideHCID 23665760Sodium Hypochlorite

Product 1

HCID 3883Lansoprazole

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]-thio]1H-benzimidazole (10 g) was suspended in 100 ml of a mixture of acetonitrile and water (7:3). A solution of sodium hydroxide was added to this suspension. 61 g of sodium hypochlorite solution (4.2%) was added over a period of 4 hours maintaining a temperature of 5° C.-10° C. Excess hypochlorite was decomposed using 3% aqueous sodium metabisulfite solution. Acetone (50 ml) was added and the pH was adjusted to between 7.5 to 8.5 using dilute acetic acid. The solids were filtered, washed with chilled water and dried in an oven to give 8 g of the title compound. The product was slurried in acetone followed by purification by dissolving in a mixture of acetone and aqueous sodium hydroxide solution. The pH of the clear solution was adjusted to about 7.0-8.0 using dilute acetic acid solution and the product was isolated by filtration, slurried in water and dried in an oven to give about 7 g of the desired product.

Workup

  1. temperaturemaintaining a temperature of 5° C.-10° C
  2. filtrationThe solids were filtered
  3. washwashed with chilled water
  4. customdried in an oven

Sources & evidence

ORD record
ord-f87b5fc15c3d4d25b49ff8adbc979eba
Source dataset
uspto-grants-2008_10
Patent number
US07439367B2

Reaction notes

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