Synthesis of deuterium- and tritium-labeled 6 beta-bromopenicillanic acid.
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.
Claes
P J
PJ
Vanderhaeghe
H
H
Roets
E
E
Thomis
J
J
De Meester
F
F
Piette
J L
JL
D055598:Chemical Phenomena; D002621:Chemistry; D003903:Deuterium; D007536:Isomerism; D010397:Penicillanic Acid / Q000138:chemical synthesis* / Q000031:analogs & derivatives; D014316:Tritium
D014316:Tritium; C018008:brobactam; D010397:Penicillanic Acid; D003903:Deuterium