Abstract: The process development and the kilogram-scale synthesis of Linrodostat presented numerous synthetic challenges (see Org. Proc. Res. Dev. 2019, 23, 2482). In this talk two stories will be highlighted, demonstrating how fundamental questions about controlling in-process impurities led to unexpected findings. These mechanistic insights then served as a starting point for the development of novel methodologies for two well-known transformations: the cleavage of the Evans oxazolidinone and amide bond formation. These methods not only impacted the successful large scale synthesis of Linrodostat, but have demonstrated relevance beyond the structure which served as inspiration for these studies.