Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Structural Biology

Background:

• Vecuronium bromide is a widely used neuromuscular blocking agent in anesthesiology since 1982.
• Detailed crystallographic and NMR analysis of its synthetic intermediates is currently lacking in scientific literature.

Purpose of the Study:

• To synthesize vecuronium bromide using modified procedures starting from epiandrosterone.
• To fill the literature gap by providing comprehensive NMR and crystallographic data for synthetic intermediates.
• To perform detailed conformational analysis of a key intermediate.

Main Methods:

• Synthesis of vecuronium bromide from epiandrosterone with procedural modifications.
• Complete assignment of 1H, 13C, and 15N NMR signals for vecuronium bromide and intermediates.
• Single-crystal X-ray diffraction and Hirshfeld surface analysis for structural and stereochemical characterization.

Main Results:

• Successful synthesis of vecuronium bromide and its advanced intermediates.
• Complete NMR signal assignment for all studied compounds.
• Detailed structural and stereochemical elucidation of 2β,16β-bispiperidino-5α-androstane-3α,17β-diol via X-ray diffraction and Hirshfeld analysis.

Conclusions:

• The study provides crucial crystallographic and NMR data for vecuronium bromide synthesis intermediates.
• This research enhances the understanding of vecuronium bromide's chemical structure and synthesis pathway.
• The findings contribute valuable information for the development and quality control of neuromuscular blocking agents.