Ammonium Hydroxide → Omeprazole

HRID 427212Notes

Reaction equation

HRID 427212 reaction equation
[OH-].[NH4+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([S@:13]([CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=3)=[O:14])[NH:10][C:9]=2[CH:26]=1>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([S:13]([CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=3)=[O:14])[NH:10][C:9]=2[CH:26]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 9568614Esomeprazole

Product 1

HCID 4594Omeprazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 50 mL beaker was added about 1 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]suffinyl]-1H-benzimidazole to 30 mL of dimethylformanide (DMF) containing 1 mL of ammonium hydroxide. Additional (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole was added to the resulting solution until a suspension of the material was formed. The solution was stirred for approximately 10 minutes, and then filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon filter. The resulting saturated solution was placed in a shallow petri dish, covered and stored under ambient conditions (approximately 25° C.) and a humidity range of 0 to 50 percent until crystals formed (between 1-4 days). The identity of the title compound is confirmed by single crystal x-ray diffraction and/or Raman spectroscopy. The resulting material was shown to contain between about 96 and 98 percent (w/w) of the 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 2 and 4 percent (w/w) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.

Workup

  1. customwas formed
  2. filtrationfiltered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon
  3. filtrationfilter
  4. customstored under ambient conditions (approximately 25° C.)
  5. customa humidity range of 0 to 50 percent until crystals formed (between 1-4 days)

Sources & evidence

ORD record
ord-f6e2bcf7f99a461aa2036650b37af566
Source dataset
uspto-grants-2001_11
Patent number
US06312723B1

Reaction notes

Loading…