Synthesis of 3H-labeled 2-hydroxy-N-[(1,3,3-trimethyl-[4,5,6-3H]cyclohexyl)methyl]-5-azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor

Article abstract of DOI:10.1002/(SICI)1099-1344(199910)42:10<965::AID-JLCR255>3.0.CO;2-K

Synthesis of ³H-labeled 2-hydroxy-N-[(1,3,3-trimethyl-[4,5,6-³H]cyclohexyl)methyli]-5-azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor, is reported. Tritiation of a mixture of N-(t-butoxycarbonyl)-1,3,3-trimethylcyclohex-4 (or 5)-enylmethylamine via T₂ and Pd/C, followed by coupling of the deprotected tritiated amine with acetyl 5-azidosalicylic acid chloride yielded the penultimate product. Subsequent deprotection and normal phase HPLC purification yielded the target compound with a radiochemical purity > 99% and a specific activity of 63 Ci/mmol.