Crystal structure of tebipenem pivoxil

The molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy) methyl (4R, 5S, 6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl) azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate), C22H31N3O6S2, has been determined and the configurations of the four chiral centers validated. The title compound crystallizes in the triclinic space group P1 with one molecule in the unit cell. Three out of the four rings adopt planar conformations while the thiazolinyl ring adopts an enveloped conformation. In the crystal, O-H center dot center dot center dot N hydrogen bonds link the molecules into chains along [1 (1) over bar0].