title: Synthesis of deuterium- and tritium-labeled 6 beta-bromopenicillanic acid.
abstract: The synthesis of 6 beta-bromopenicillanic acid labeled with deuterium and tritium in the beta-methyl group is described. The S-sulfoxide of benzyl- or p-methoxybenzyl 6 alpha-bromopenicillanate is refluxed in benzene containing an excess of tert-BuOD, D2O or HTO. After deoxygenation and deprotection of the ester, the labeled 6 alpha-bromopenicillanic acid is epimerized (N,O-bis(trimethylsilyl)acetamide/1,5-diazabicyclo[4.3.0]non-5-ene in CH2Cl2). The two epimers are separated by column chromatography.
authors.forename: P J
authors.initials: PJ
authors.lastname: Claes
authors.forename: H
authors.initials: H
authors.lastname: Vanderhaeghe
authors.forename: E
authors.initials: E
authors.lastname: Roets
authors.forename: J
authors.initials: J
authors.lastname: Thomis
authors.forename: F
authors.initials: F
authors.lastname: De Meester
authors.forename: J L
authors.initials: JL
authors.lastname: Piette
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D003903:Deuterium; D007536:Isomerism; D010397:Penicillanic Acid / Q000138:chemical synthesis* / Q000031:analogs & derivatives; D014316:Tritium
chemical_list: D014316:Tritium; C018008:brobactam; D010397:Penicillanic Acid; D003903:Deuterium