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Precursor of a β‐lactamase inhibitor: allyl (4S,8S,9R)‐10‐[(E)‐ethyl­idene]‐4‐methoxy‐11‐oxo‐1‐aza­tri­cyclo­[7.2.0.03,8]­undec‐2‐ene‐2‐carboxyl­ate
Authors:Ivan Leban  Lovro Seli   Toma Mesar  Anton opar  Tom &#x;olmajer
Institution:Ivan Leban,Lovro Seli?,Toma? Mesar,Anton ?opar,Tom ?olmajer
Abstract:The molecular structure of the title tricyclic compound, C17H21NO4, which is the immediate precursor of a potent synthetic inhibitor {Lek157: sodium (8S,9R)‐10‐(E)‐ethyl­idene]‐4‐methoxy‐11‐oxo‐1‐aza­tri­cyclo­7.2.0.03,8]­undec‐2‐ene‐2‐carboxyl­ate} with remarkable potency, provides experimental evidence for the previously modelled relative position of the fused cyclo­hexyl ring and the carbonyl group of the β‐lactam ring, which takes part in the formation of the initial tetrahedral acyl–enzyme complex. In this hydro­phobic mol­ecule, the overall geometry is influenced by C—H?O intramolecular hydrogen bonds 3.046 (4) and 3.538 (6) Å, with corresponding normalized H?O distances of 2.30 and 2.46 Å], whereas the mol­ecules are interconnected through intermolecular C—H?O hydrogen bonds 3.335 (4)–3.575 (5) Å].
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