Synthesis of unlabelled and stable‐isotope–labelled glucuronide metabolites of dapagliflozin and synthesis of stable‐isotope–labelled dapagliflozin

Two regioisomeric glucuronide metabolites of dapagliflozin (BMS‐512148) were synthesized and used to elucidate the structures of dapagliflozin metabolites observed in human urine samples. The structures of the synthetic metabolites were assigned by heteronuclear multiple‐bond correlation, ROESY, and total correlation spectroscopy experiments. Analogues of these metabolites containing carbon‐13 as a stable label were also prepared for use as internal standards for the analysis of urine samples obtained from patients participating in clinical studies.