Preparation of 11COCl2

Briνkman, G. A.; Haas-Lisewska, I.; Veenboer, J.Th.; Lindner, L.

doi:10.1016/0020-708x(78)90114-x

Cited by 29 publications

(20 citation statements)

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“…Use of a different dipolar aprotic non-nucleophilic solvent, namely THF, produced a high yield of the target unsymmetrical urea [ 11 2, entries 7 and 8). DMF is known to react with carbonyl difluoride to produce carbon dioxide in a difluoro-decarbonylation reaction.…”

Section: Resultsmentioning

confidence: 99%

“…[5] Principal, among these secondary agents, is [ 11 C]iodomethane for labelling at a non-metal heteroatom (e. g., N, O, and S) with a [ 11 C]methyl group. [5c] [ 11 C]Carbon monoxide has featured widely for labelling carbonyl functionality. [6] However, not all potential radiotracers have structures that may be labelled either efficiently or at all by existing methods.…”

Section: Introductionmentioning

confidence: 99%

“…[16] In this method, [ 11 C]carbonyl difluoride is produced reliably in useful overall radiochemical yield and with high nocarrier-added (NCA) molar activity (> 200 GBq/μmol). This new labelling agent has been shown to be very effective for 11 Ccarbonylation reactions giving intracyclic ureas, as especially exemplified by the synthesis of a β-adrenergic receptor imaging agent, [ 11 C](S)-CGP12177. [16] Here we aimed to further explore NCA [ 11 C]carbonyl difluoride as a labelling agent for acyclic ureas, especially unsymmetrical ureas.…”

Section: Introductionmentioning

confidence: 99%

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Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

Jakobsson

Telu

et al. 2021

Chemistry A European J

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Effective methods are needed for labelling acyclic ureas with carbon-11 (t 1/2 = 20.4 min) as potential radiotracers for biomedical imaging with positron emission tomography (PET). Herein, we describe the rapid and high-yield syntheses of unsymmetrical acyclic [ 11 C]ureas under mild conditions (room temperature and within 7 min) using no-carrier-added [ 11 C]carbonyl difluoride with aliphatic and aryl amines. This methodology is compatible with diverse functionality (e. g., hydroxy, carboxyl, amino, amido, or pyridyl) in the substrate amines. The labelling process proceeds through putative [ 11 C]carbamoyl fluorides and for primary amines through isolable [ 11 C]isocyanate intermediates. Unsymmetrical [ 11 C]ureas are produced with negligible amounts of unwanted symmetrical [ 11 C]urea byproducts. Moreover, the overall labelling method tolerates trace water and the generally moderate to excellent yields show good reproducibility. [ 11 C]Carbonyl difluoride shows exceptional promise for application to the synthesis of acyclic [ 11 C]ureas as new radiotracers for biomedical imaging with PET.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

Jakobsson

Telu

et al. 2021

Chemistry A European J

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“…The well-known b-adrenoceptor radioligand, [ 11 C](S)-CGP 12177, [30,31] was obtained in 72 AE 15 % yield with very little side product formation (see Supporting Information), despite the presence of a secondary amino and secondary alcohol group. Carbon-11 produced with a cyclotron by the 14 N-(p,a) 11 [32] and had been inaccessible through selenium-mediated carbonylation with [ 11 C]CO 2 . [12] [ 11 C]DMO ([ 11 C]17), a PET radiotracer useful for determining tissue pH in vivo, was synthesized from a hydroxy propionamide precursor.…”

Section: Angewandte Chemiementioning

confidence: 99%

[¹¹C]Carbonyl Difluoride—a New and Highly Efficient [¹¹C]Carbonyl Group Transfer Agent

Jakobsson

Telu

et al. 2020

Angew Chem Int Ed

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Herein, the synthesis and use of [ 11 C]carbonyl difluoride for labeling heterocycles with [ 11 C]carbonyl groups in high molar activity is described. A very mild single-pass gasphase conversion of [ 11 C]carbon monoxide into [ 11 C]carbonyl difluoride over silver(II) fluoride provides easy access to this new synthon in robust quantitative yield for labeling a broad range of cyclic substrates, for example, imidazolidin-2-ones, thiazolidin-2-ones, and oxazolidin-2-ones. Labeling reactions may utilize close-to-stoichiometric precursor quantities and short reaction times at room temperature in a wide range of solvents while also showing high water tolerability. The overall radiosynthesis protocol is both simple and reproducible. The required apparatus can be constructed from widely available parts and is therefore well suited to be automated for PET radiotracer production. We foresee that this straightforward method will gain wide acceptance for PET radiotracer syntheses across the radiochemistry community.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…The direct proton irradiation of ammonia containing nitrous oxide yields about a 30% yield of [ u C]-guanidine [90,91]. Bombardment of a nitrogen gas target containing a mixture of carbon monoxide and chlorine gas was reported as a direct source of f 11 C]-phosgene [92], However, modified synthetic techniques are more amenable to routine production requirements [93,94].…”

Section: Ch 3 1 Preparationmentioning

confidence: 99%

The Chemistry of Positron Emitting Nucleogenic (Hot) Atoms with Regard to Preparation of Labelled Compounds of Practical Utility

Ferrieri

Wolf

1983

Radiochimica Acta

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Preparation of 11COCl2

Cited by 29 publications

References 1 publication

Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

[¹¹C]Carbonyl Difluoride—a New and Highly Efficient [¹¹C]Carbonyl Group Transfer Agent

The Chemistry of Positron Emitting Nucleogenic (Hot) Atoms with Regard to Preparation of Labelled Compounds of Practical Utility

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Preparation of 11COCl2

Cited by 29 publications

References 1 publication

Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [11C]Ureas for Biomedical Imaging from [11C]Carbonyl Difluoride

Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [11C]Ureas for Biomedical Imaging from [11C]Carbonyl Difluoride

[11C]Carbonyl Difluoride—a New and Highly Efficient [11C]Carbonyl Group Transfer Agent

The Chemistry of Positron Emitting Nucleogenic (Hot) Atoms with Regard to Preparation of Labelled Compounds of Practical Utility

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Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [¹¹C]Ureas for Biomedical Imaging from [¹¹C]Carbonyl Difluoride

[¹¹C]Carbonyl Difluoride—a New and Highly Efficient [¹¹C]Carbonyl Group Transfer Agent