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Synthesis of tritium labelled mecillinam
Author(s) -
Frederiksen Søren Melsing,
GrueSørensen Gunnar
Publication year - 2003
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.717
Subject(s) - mecillinam , chemistry , tritium , lactam , trimethylsilyl , stereochemistry , radiochemistry , medicinal chemistry , enterobacteriaceae , biochemistry , escherichia coli , physics , nuclear physics , gene
The potent β ‐lactam antibiotic mecillinam has successfully been labelled with tritium. 2,3,4,7‐Tetrahydro‐1H‐azepin‐1‐carbaldehyde was formed in a ring‐closing metathesis reaction and then condensed with trimethylsilyl protected penicillanic acid to give dehydro‐mecillinam. Pd/C catalysed tritiation then gave [ 3 H 2 ]‐mecillinam (6‐ β (([3,4‐ 3 H 2 ]hexahydro‐1H‐azepin‐1‐yl)methyleneamino)penicillanic acid) with a radiochemical purity of 96% and a specific activity of 24 Ci/mmol. Copyright © 2003 John Wiley & Sons, Ltd.