167569-09-7

Basic information

• Product Name: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine
• CAS NO: 167569-09-7
• Molecular Formula: C₉H₁₀¹⁸FNO₄
• Molecular Weight: 214.1809
• Mol File: 167569-09-7.mol

Chemical Properties

• Density: 1.553g/cm³
• Refractive Index: 1.629
• CAS DataBase Reference: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(167569-09-7)
• EPA Substance Registry System: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(167569-09-7)

Safety Data

• Hazardous Substances Data: 167569-09-7(Hazardous Substances Data)

Upstream product

• 63-84-3 dopa 
• 1206189-95-8 ⁽¹⁸⁾F-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2'-fluoro-4'-methoxybenzyl)-(2R,5S)-pyrazine-5'-formate 
• 1644527-25-2 C₂₃H₃₄⁽¹⁸⁾FNO₈ 
• 5796-17-8 D-Dopa 
• 1614253-58-5 (S)-tert-butyl-(S)-2-(tritylamino)-3-(5-formyl-4-methoxymethoxy-2-nitro-phenyl)-propionate 
• 59-92-7 levodopa 
• 129841-03-8 3,4-methylenedioxy-6-[18F]flourobenzyl bromide 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 

Downstream Products

• 92812-82-3 [18F]-L-3,4-dihydroxy-6-fluorophenylalanine 

Relevant articles and documents

Trifluoromethanesulfonic acid, an alternative solvent medium for the direct electrophilic fluorination of DOPA: New syntheses of 6-[18F]fluoro- L-DOPA and 6-[18F]fluoro-D-DOPA

Previous work from this laboratory has shown that the direct fluorination of 3, 4-dihydroxy-phenyl-L-alanine (L-DOPA) in anhydrous HF (aHF) or BF 3/HF with F2 is an efficient method for the synthesis of 6-fluoro-L-DOPA. Since then, 18F-labeled 6-fluoro-L-DOPA ([ 18F]6-fluoro-L-DOPA) has been used to study presynaptic dopaminergic function in the human brain and to monitor gastrointestinal carcinoid tumors. This work demonstrates that the reactivity and selectivity of F2 toward L-DOPA in CF3SO3H is comparable with that in aHF. This new synthetic procedure has led to the production of [18F] fluoro-L-DOPA and [18F]fluoro-L-DOPA isomers in 17 ± 2% radiochemical yields (decay corrected with respect to [18F]F 2). The 2- and 6-FDOPA isomers were separated by HPLC and subsequently characterized by 19F NMR spectroscopy. The corresponding [18F]-FDOPA enantiomers have been obtained in clinically useful quantities by a synthetic approach that avoids the use of aHF. Copyright

One-pot synthesis of high molar activity 6-[18F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor

A one-pot two-step synthesis of 6-[18F]fluoro-l-DOPA ([18F]FDOPA) has been developed involving Cu-mediated radiofluorination of a pinacol boronate ester precursor. The method is fully automated, provides [18F]FDOPA in good

Synthesis of 6-[11C]methyl-m-tyrosine ([11C]6MemTyr) for dopamine synthesis imaging in living brain using PET

A novel PET probe, 6-[11C]methyl-m-tyrosine ([11C]6MemTyr), was developed for quantitative imaging of presynaptic dopamine (DA) synthesis in the living brain using positron emission tomography (PET). This probe was evaluated by comparison with conventional 6-[18F]fluoro-l-dopa ([18F]FDOPA). [11C]6MemTyr was labeled using rapid Pd(0)-mediated C-[11C]methylation with [11C]methyl iodide. The synthesis time was only 35 min, and its radiochemical yield was 76%, with radiochemical purity of >99%. PET measurements indicated that [11C]6MemTyr could image presynaptic DA synthesis in the striatum of living monkey brain, providing much higher contrast between the striatum and the cerebellum than that with [18F]FDOPA.

The effect of aromatic fluorine substitution in L-DOPA on the in vivo behaviour of [18F]2-, [18F]5- and [18F]6-fluoro-L-DOPA in the human brain

Remarkable differences in the human in vivo behaviour of each of the three [18F]-labelled ring fluorinated isomers of L-dihydroxyphenylalanine (L-DOPA) are presented. Unlike [18F]2-fluoro-L-DOPA, which did not appear to cross the blood brain barrier, [18F]5-fluoro-L-DOPA appears to be taken up and cleared from the cerebellum and the striata. In contrast with the 2- and 5-fluoro isomers of L-DOPA, radioactivity derived after injection of [18F]6-fluoro-L-DOPA is specifically retained in the striata. The present study is the first direct comparison of the time course and distribution of radioactivity in the human brain after intravenous injections of [18F]2-, [18F]5- and [18F]6-fluoro-L-DOPA.

Use of SF6 for the production of electrophilic 18F-fluorination reagents

Electrophilic 18F-fluorination is an important method for production of tracers for positron emission tomography. The most commonly employed 18F-fluorination reagents [18F]F2, [18F]Selectfluor bis(tri

Cu-Mediated Radiofluorination of Aryl Pinacolboronate Esters: Alcohols as Solvents with Application to 6-L-[18F]FDOPA Synthesis

Cu-mediated radiofluorination of arylboronic acid pinacol esters (ArylBPin) using Cu(OTf)2(Py)4 complex is a useful approach for the introduction of [18F]fluorine into non-activated arenes and heteroarenes. Owing to the co

Direct arene C–H fluorination with 18F? via organic photoredox catalysis

Positron emission tomography (PET) plays key roles in drug discovery and development, as well as medical imaging. However, there is a dearth of efficient and simple radiolabeling methods for aromatic C–H bonds, which limits advancements in PET radiotracer

L-dopa precursor compound, preparation method thereof, and preparation method of 18F labeled L-dopa using the same

The present invention relates to an L-dopa precursor compound, a preparation method thereof, and a preparation method of an ^18F labeled L-dopa using the same. The preparation method of the ^18F labeled L-dopa comprises a step of preparing a compound repr

Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion

As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[18F]fluoro-3,4-dihydroxy-L-phenylalanine ([18F]FDOPA) using the nucleophilic [18F]F- process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodonium salt precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [18F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27–38 % RCY d.c. (n = 5), >99 % RCP, >99 % ee., and high Am 170–230 GBq/μmol. In addition, this optimization study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabeling process to achieve high fluorine-18 incorporation yields.

Novel preparation method for positron medicine [18F]FDOPA and intermediate thereof

The invention relates to a novel preparation method for a positron medicine [18F]FDOPA and an intermediate thereof, and in particular to a synthesis method for [18F]FDOPA. The preparation method includes the following steps: (img file ='DDA0001356857630000011.TIF' wi='1718' he='312'/) (1) a compound as formula I reacts with an appropriate 18F source to generate a compound as formula II; (2) the compound as formula II undergoes deprotection operation to generate [18F]FDOPA; R1 and R2 are respectively hydroxyl protecting groups; R3 is chosen from any one of halogen-substituted alkyl group and aryl group, or two R3s are formed together into a 5-8-membered ring; R4 is a carboxyl protecting group; and R5 an R6 are respectively chosen from H and an amino protecting group.