(3S,5R,6S)-Di-phenyl-methyl 1-oxo-6-bromo-penicillanate

Area of Science:

• Medicinal Chemistry
• Crystallography
• Organic Chemistry

Background:

• Tazobactam is a crucial beta-lactamase inhibitor widely used in clinical practice.
• Understanding the structure of its synthetic intermediates is vital for process optimization and drug development.

Purpose of the Study:

• To elucidate the three-dimensional structure of a key intermediate in tazobactam synthesis.
• To characterize the conformational properties of the thia-zolidine and azetidine rings.
• To identify non-covalent interactions within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
• Conformational analysis of the heterocyclic rings was performed.
• Intermolecular interactions, including hydrogen bonds and C-H⋯π interactions, were analyzed.

Main Results:

• The crystal structure of the title compound (C21H20BrNO4S) was successfully determined.
• The five-membered thiazolidine ring adopts an envelope conformation.
• The four-membered azetidine ring exhibits a distorted planar conformation.
• Weak C-H⋯O hydrogen bonds and a C-H⋯π interaction were identified as significant crystal packing forces.

Conclusions:

• The determined crystal structure provides valuable insights into the stereochemistry of the tazobactam intermediate.
• The conformational preferences of the rings and the identified weak interactions are important for understanding the solid-state properties and potential reactivity.
• This structural information can aid in the design of improved synthetic routes for tazobactam.