Synthesis of 14C-labelled (R)-α-amino-6,7-dimethyl-3-(phosphonomethyl)-2-quinolinepropanoic acid

Swahn, Britt‐Marie; Андерссон, Фредрик; Pelcman, Benjamin; Söderberg, Johan; Claesson, Alf

doi:10.1002/(sici)1099-1344(199703)39:3<259::aid-jlcr968>3.0.co;2-e

Cited by 11 publications

(6 citation statements)

References 4 publications

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“…This approach has since been successfully adapted and employed by several groups for the synthesis of other pyridylalanine derivatives, 10-15 and extended to the synthesis of related heterocyclic derivatives. 16,17 Different groups have commented, 11, 19 in short communications, upon the reliability of the methods available for formation of the organozinc reagents needed for these coupling reactions, and given our recent advances in this area, [20][21][22] we now report, in full, the results of a systematic study of methods for the synthesis of a range of substituted pyridylalanine derivatives. In the context of a study to assess the use of pyridyl amino acids as chiral DMAP analogues, [23][24][25][26] we have considered the synthesis of amino-substituted pyridine derivatives, to be used as components of potentially catalytically active peptides.…”

Section: Introductionmentioning

confidence: 99%

Preparation of enantiomerically pure pyridyl amino acids from serine

2003

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A range of substituted pyridyl amino acids have been prepared by palladium catalysed cross-coupling of serine-derived organozinc reagents with differently substituted halopyridines. Following this procedure a DMAP analogue has been synthesised and used as a building block in the preparation of two related tripeptides, which have been tested as catalysts in the kinetic resolution of trans-2-(N-acetylamino)cyclohexan-1-ol, resulting in modest enantioselectivity.

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Section: Introductionmentioning

confidence: 99%

Preparation of enantiomerically pure pyridyl amino acids from serine

2003

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“…Reagent based cross-coupling reactions in radiosynthesis, however are still somewhat rare. For example, the carbon-14 methylation of aryl halides and triflates with ( 14 CH 3 ) 2 Zn / NiCl 2 [34] and 14 CH 3 BR 2 / Pd o [35] and carbonylations using small quantitites of 14 CO [75] have only recently been described. Cyanide cross-coupling reactions however, are more common and provide convenient access to aryl [ 14 C]cyanides.…”

Section: [ 14 C]methyl Iodidementioning

confidence: 95%

Recent Advances in the Design and Synthesis of Carbon-14 Labelled Pharmaceuticals from Small Molecule Precursors

McCarthy

2000

CPD

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Over the past decade, the increased chemical complexity of new drug candidates has resulted in a parallel need to develop innovative syntheses of carbon-14 labelled pharmaceuticals. Faced with short time-lines and a limited number of labelled precursors, radiochemists have addressed this challenge by developing new reagents and adapting existing technology to labelled syntheses. Selected examples from the recent radiochemical literature illustrate some of the creative strategies used to rapidly solve these synthetic challenges. Examples describing the handling and use of common small molecule reagents, such as carbon-14 labelled carbon dioxide, methyl iodide, cyanide, acetic acids, sulfur and phosphorous stabilized ylides for the synthesis of labelled steroids, prostanoids, nucleosides, pyridines, quinolines, benzazepines and other heterocycles are presented. Several general strategies for radiolabelling are also discussed including the degradation strategy for accessing necessary intermediates and precursors, the radiolabelling of aromatic substrates, transition metal mediated cross-couplings, and the use of chiral auxiliaries for the enantioselective syntheses of radiolabelled pharmaceuticals.

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“…Negishi cross‐coupling of 2,6‐dibromoquinoline 28 with zinc reagent using Pd(OAc) 2 /P( o ‐furyl) 3 catalyst mixture in toluene/DMA afforded a 2‐substituted quinoline derivative 29 (Scheme 8) . The latter was, in turn, subjected to nickel‐catalyzed cross‐coupling with 14 C‐labeled methylzinc iodide to afford the radiolabeled N ‐methyl‐ D ‐aspartate (NMDA) antagonist, 3‐(diethoxyphosphonomethyl)quinoline derivative 30 , in 37% yield.…”

Section: Application Of Cross‐coupling Reactions In the Synthesis Of mentioning

confidence: 99%

Halogenated Quinolines as Substrates for the Palladium‐Catalyzed Cross‐Coupling Reactions to Afford Substituted Quinolines

Mphahlele

Lesenyeho

2013

Journal of Heterocyclic Chem

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View this article online at wileyonlinelibrary.com.The use of palladium complexes in catalyzing the cross-coupling of halogenated quinolines with various organometalic reagents has led to the development of radically new methods of synthesizing novel substituted quinoline derivatives. The focus of this review is on the application of the following palladium-catalyzed reactions of halogenated quinolines with organometalic reagents to afford substituted quinoline derivatives: Kumada, Stille, Negishi, Sonogashira, Suzuki, Heck, and Hiyama cross-coupling reactions. Scheme 4. Palladium-catalyzed coupling of the 4-bromoquinoline derivatives with zinc cyanide. Reagents and conditions: (i) Zn(CN) 2 , Pd(PPh 3 ) 4 , DMF, 80°C; (ii) Pyr·HBr, 200°C. Scheme 3. Palladium-catalyzed Negishi cross-coupling of quinolyl zinc iodides with organoiodides. Reagents and conditions: (i) Zn, DMA; (ii) Pd(dba) 2 , P(o-furyl) 3 , THF, room temperature or heat (for 13c, e, and f).4 M. Scheme 8. Successive Negishi cross-coupling of 2,6-dibromoquinoline with organozinc reagents. Reagents and conditions: (i) Pd(OAc) 2 , P(o-furyl) 3 , PhMe/DMA; (ii) [ 14 C]-MeZnI; NiCl 2 (dppp); THF. Scheme 9. Palladium-phosphinous acid-catalyzed alkynylation of 4-chloroquinoline. Reagents and conditions: (i) POPd, TBAB, NaOH, CuI, H 2 O, 5 h. Scheme 10. One-pot palladium/CuI-catalyzed dialkynylation of 2,4-dichloroquinoline. Reagents and conditions: (i) Pd/C, PPh 3 , CuI, NEt 3 , water, 80-85°C. 6 M.

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Synthesis of 14C-labelled (R)-α-amino-6,7-dimethyl-3-(phosphonomethyl)-2-quinolinepropanoic acid

Cited by 11 publications

References 4 publications

Preparation of enantiomerically pure pyridyl amino acids from serine

Preparation of enantiomerically pure pyridyl amino acids from serine

Recent Advances in the Design and Synthesis of Carbon-14 Labelled Pharmaceuticals from Small Molecule Precursors

Halogenated Quinolines as Substrates for the Palladium‐Catalyzed Cross‐Coupling Reactions to Afford Substituted Quinolines

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