Doultegravir 2-F Impurity C

Dolutegravir 2-F Impurity C is a fluorinated synthetic byproduct arising from the substitution of a hydrogen atom at the 2-position of the benzene ring in the dolutegravir scaffold. It retains the core pyridone-based structure but lacks the terminal sulfonamide group, featuring a hydroxylated ester moiety instead. The fluorine substitution introduces steric and electronic perturbations, altering metabolic stability. This impurity is generated during late-stage synthesis via nucleophilic aromatic substitution pathways. It serves as a critical HPLC reference standard for quantifying process-related impurities in dolutegravir drug substance batches.