Chemical Reactions of Omeprazole and Omeprazole Analogues. V. The Reaction of N-Alkylated Derivatives of Omeprazole Analogues with 2-Mercaptoethanol.

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Abstract
Omeprazole, 5-methoxy-2-(4-methoxy-3,5-dimethyl-2-pyridinylmethylsulfinyl)-1H-benzimidazole, analogues substituted on the benzimidazole nitrogen, but lacking the methoxy group in the benzimidazole part, have been studied. In dilute HCl (in the absence of 2-mercaptoethanol, H.beta.) the N-methylated analogue is much more stable than omeprazole (INN name). The results obtained in the presence of H.beta. have been used to show that an acid-catalyzed attack of H.beta. on the sulfenamide (D+) from omeprazole is the major reaction in the formation of the disulfide HE.beta.+ in 0.1 M HCl and that the direct reaction to HE.beta.+ from the sulfenic acid HC+ is of minor importance. The interconversion of two diasteromeric N-alkylated compounds has also been studied.

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