Chemical Properties
Brown to Purple Solid
Uses
Pantoprazole Sulfone (Pantoprazole EP Impurity A) is a metabolite of Pantoprazole (P183000), an antiulcerative, gastric pump inhibitor. Pantoprazole USP Related Compound A.
Definition
ChEBI: 1H-Benzimidazole, 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfonyl]- is a member of benzimidazoles and a sulfoxide.
Synthesis
Pantoprazole impurity A was prepared as follows: 237 mg (815 mol) of S-dichloro chiral ligand, 95.8 mg (271 mol) of ferric triacetylacetonate (Iron(III) acetylacetonate), and the lithium salt of 4-dimethylamino benzoic acid, 23.4 mg (137 mol), were suspended at 25 C in 5 mL of ethyl acetate and stirred for more than 30 minutes. 1.00 g (2.72 mmol) of the sulfide structure of pantoprazole and 5 mL of ethyl acetate were added. After cooling the mixture to -8C at a cooling rate of 1C per minute, 556 L (5.44 mol) of a 30% aqueous hydrogen peroxide solution was added dropwise over 1 min. After 44 h, the reaction mixture was analyzed by HPLC analysis condition 2 as well as HPLC analysis condition 3. Containment: 75% of the sulfoxide structural body; 13% of the sulfone structural (pantoprazole impurity A) body; and 12% of the sulfide structural body.
