- Efficient H-D exchange of aromatic compounds in near-critical D2O catalysed by a polymer-supported sulphonic acid
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Hydrogen atom exchange of aromatic compounds in neutral near-critical D2O has been improved by using a polymer-supported sulphonic acid catalyst. Phenol, aniline, quinoline, and substituted aromatic hydrocarbons are selectively ring-perdeuterated in high yields with insignificant by-product formation at 325 °C for 24 h in D2O/Deloxan.
- Boix, Carmen,Poliakoff, Martyn
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p. 4433 - 4436
(2007/10/03)
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- The synthesis of labelled forms of saquinavir
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The development of the HIV-protease inhibitor, saquinavir (Ro 31-8959), required a range of analytical methods for the measurement of the parent drug and drug-related material in biological fluids. This paper describes the synthesis of 14-carbon and tritium labelled compounds used for in vivo and in vitro investigations of the absorption and disposition of saquinavir in animals and man. It also discusses the preparation of saquinavir labelled with deuterium and stable isotopes of carbon and nitrogen. These forms of the drug were needed for bioequivalence studies in which HPLC/MS/MS was employed for the measurement of plasma concentrations. Finally, the synthesis of a 125-iodine labelled tracer used in a radioimmunoassay for saquinavir is described.
- Wiltshire,Prior,Dhesi,Trach,Schlageter,Schoenenberger
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p. 1103 - 1126
(2007/10/03)
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- Synthesis of polydeuterated benzothiazoles via supercritical deuteration of anilines
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2-[2H]Benzothiazole, readily available according to the literature, was observed to undergo slow isotope exchange in water. This necessitated development of practical syntheses for benzothiazoles carrying deuterium labels in positions other than 2. [4,5,6,7-2H4]Benzothiazole and 4-[2H3]methyl[5,6,7-2H3]benzothiazole were prepared in good yields from [2H7]aniline and 2-[2H9]toluidine, which were obtained by novel rapid isotope exchange in supercritical deuterium oxide.
- Junk, Thomas,Catallo, W. James,Civils, L. Dana
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p. 625 - 630
(2007/10/03)
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- Preparative supercritical deuterium exchange in arenes and heteroarenes
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Deuterated homo- and heterocyclic aromatic substrates bearing various functionalities were prepared by isotope exchange in supercritical deuterium oxide, with little or no formation of byproducts. Equilibration was attained rapidly (1-24 hrs), and deuterium exchange extended to alpha positions of alkyl homologs. Nitro- and haloarenes, thioethers, telluroethers, and some heterocyclic substrates were unstable.
- Junk, Thomas,Catallo, W. James
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p. 3445 - 3448
(2007/10/03)
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