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Marshall, Jonathan; Ayers, Sloan; Beutner, Gregory L.; Sfouggatakis, Christopher
Tetrahedron letters, 06/2024, Letnik: 142Journal Article
Display omitted •Identification of an unknown byproduct generated in Curtius rearrangement reaction in the synthesis of BMS-986020.•Impurity was isolated by reverse phase semi-preparative HPLC and identified by a combination of high resolution mass spectrometry and NMR. BMS-986020 was developed as an antagonist of the LPA1 receptor for the treatment of lung fibrosis (Idiopathic Pulmonary Fibrosis (IPF)). During the development of BMS-986020, a high percentage byproduct was observed in the mother liquor of a Curtius rearrangement reaction. The structure identification and formation mechanism of this unknown byproduct was deemed necessary to understand for further the reaction optimization and knowledge generation for the project. The characterization process required a multifaceted approach utilizing LC-HRMS, VT-NMR, and HPLC isolation. The investigation’s final result implicated the reaction base as the root cause of the byproduct formation and indicated a nitrene-iminium reaction pathway to form the byproduct.
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Leto | Faktor vpliva | Izdaja | Kategorija | Razvrstitev | ||||
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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