Notes- Synthesis of Benzyl Vinylcabamate and 3-O-Vinylcarbamoyl-D-mannitol Pentanitrate

Wolfrom, M. L.; McFadden, G; Chaney, Alan

doi:10.1021/jo01351a644

Cited by 13 publications

(19 citation statements)

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“…Methyl glyoxylate (4) and benzyl vinylcarbamate (5) were prepared according to the literature. 13,14 Solid phase columns were purchased from Merck (Lichrolut EN). Analytical thin layer chromatography (TLC) was performed using plates from Merck (Silicagel 60 F 254 ).…”

Section: Generalmentioning

confidence: 99%

“…The crude product was separated by column chromatography (ethyl acetate) to yield 5.9 g (15 mmol, 76%) of 13. (14). To a stirred solution of 110 mg (0.37 mmol) triphosgene in 4 ml dry dichloro methane at 08C under argon atmosphere were slowly added, over a period of 30 min, a solution of 400 mg (1 mmol) 13 and 189 ml (1.1 mmol) N-ethyldiisopropylamine in 3.5 ml dry dichloro methane.…”

Section: -[4-(2-fluoroethyl)-piperazin-1-yl]-phenylamine (10) 40 G mentioning

confidence: 99%

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Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Piel¹,

Schirrmacher²,

Höhnemann³

et al. 2003

Labelled Comp Radiopharmac

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The neurotransmitter glutamate is thought to be crucially involved in a huge number of neurological and psychiatric disorders, such as Morbus Parkinson, Alzheimer's disease and schizophrenia. Aiming at an improved diagnostic tool for PET a new [18F]fluorine labelled NMDA receptor ligand was developed that may potentially allow the in vivo visualization of glutama‐tergic neurotransmission. The 19F‐analogue trans‐5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydro quinoline‐2‐carboxylic acid was synthesised to determine the binding affinity, lipophilicity and biodistribution of the ligand. This substance exhibits a Ki of 12 nM for the glycine binding site using [3H]MDL‐105,519 assays on pig cortical membranes. A logD of 1.3 was determined for this compound according to the OECD guidelines employing the HPLC method. Radiosynthesis of this ligand was achieved by labelling the precursor trans‐5,7‐dichloro‐4‐[3‐(4‐piperazin‐1‐yl‐phenyl)‐ureido]‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid methyl ester with 2‐[18F]fluoroethyltosylate and subsequent cleaving of the methyl ester moiety, resulting in an overall decay corrected yield of 35% of the final product trans‐5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[18F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid. The biodistribution kinetics of this compound were determined with Sprague Dawley rats ex vivo for brain, liver, kidney, and bone. The ligand showed a maximum brain uptake 30 min.p.i. of about 0.1% ID/g. Copyright © 2003 John Wiley & Sons, Ltd.

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Section: Generalmentioning

confidence: 99%

Section: -[4-(2-fluoroethyl)-piperazin-1-yl]-phenylamine (10) 40 G mentioning

confidence: 99%

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Piel¹,

Schirrmacher²,

Höhnemann³

et al. 2003

Labelled Comp Radiopharmac

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“…127 ,O 5.5' 21,7 126,6 6,6' 144,O 6 7,7', l1,11' 130,l 159,8 7,11 129,6 8,S', 10,lO' 128,8 160,O 8,lO 128,7 9.9' 128,2 160,s 9 128, 5 12 154 Im 'H-rauschentkoppelten I3C-Spektrum von 2 (s. Tab. 1) findet man neben den beiden Methyl-C-Signalen bei 23,9 und 21,7 ppm und den Methin-C-Signalen der zwei aquivalenten Phenylringe bei 130,l (ortho), 128,s (meta) und 128,2 ppm (para) vier Signale von quaternaren C-Atomen bei 154, 8,144,0,135,6 und 129,5 ppm. Das Signal bei 154,s ppm bleibt im unentkoppelten 13C-Spektrum ein scharfes s und muss deshalb C (12) zugeordnet werden; die chemische Verschiebung von 154,s ppm ist im Einklang mit einer Harnstoffgruppierung [4].…”

unclassified

“…Das Der zu 6 analoge Phenylgruppen-freie Komplex der Formel 9 (Smp. 102-103"; ClIH6Fe2N207) wurde in 1,9% Ausbeute bei der Umsetzung von Vinylisocyanat (8) [8] bei 3,48 und 3,34 ppm zwei s fur die zwei CH30-und bei 1,69 und 1,16 ppm zwei s fur =C (CH,),"). Im 'H-rauschentkoppelten I3C-NMR.-Spektrum (Tab.…”

unclassified

“…0,2168 (24) 0,4590 (21) 0,5149 ( 2 0 ) 0,5209 ( 2 3 ) 0,6417 (20) 0,8999 (30) 0,5335 (29) 0,5767 (26) 0,6395 (11) 0,3768 (25) 0,1746 (27) 0,4230 (28) 0,2620 (26) 0,2186 ( 2 ) 0,3332 (1) 0,0723 (12) 0,2890 (12) 0,1728 (12) 0,3269 ( 1 2 ) 0,4466 (14) 0,4487 (12) 0,4050 (10) 0,3232 ( 9 ) 0,2179 ( 9 ) 0,1224 (8) 0,2263 ( 7 ) 0,2423 (14) 0,1846 (10) 0,1434 (19) 0,1819 (10) 0,1269 (10) 0,1420 (17) 0,1003 (15) 0,0305 (16) 0,0079 (15) 0,0578 (13) 0,2409 (11) 0,3077 ( 1 2 ) 0,1920 (12) 0,3520 (12) 0,3599 ( 1 5 ) 0,0770 (15) 0,1296 (14) 0,2405 (6) 0,1923 (14) 0,3258 (13) 0,4001 (14) 0,4018 (13) 0,0735 (1) 0,0602 ( 1 ) 0,0594 ( 7 ) 0,1198 ( 7 ) 0,1495 ( 7 ) 0,1184 ( 7 ) 0,1165 ( 7 ) -0,0019 ( 7 ) -0,0094 ( 6 ) 0,0249 ( 6 ) -0,0465 ( 6 ) -0,0261 ( 4 ) 0,0309 ( 4 ) -0,0535 (7) -0,0194 ( 5 ) -0,0294 (10) 0,0186 ( 6 ) 0,0521 (6) 0,0744 ( 9 ) 0,1070 ( 8 ) 0,1161 ( 9 ) 0,0914 ( 9 ) 0,0586 ( 8 ) 0,0107…”

unclassified

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Stickstoffhaltige Dieisen‐hexacarbonyl‐Komplexe aus 3‐Phenyl‐2H‐azirinen

Nakamura

Bachmann

Heimgartner

et al. 1978

Helvetica Chimica Acta

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Nitrogen‐containing diiron‐hexacarbonyl complexes from 3‐phenyl‐2H‐azirines Reaction of 2,2‐dimethyl‐3‐phenyl‐2H‐azirine (1) with diiron‐enneacarbonyl yields as an insertion product, and in addition to other products, the diiron‐hexacarbonyl complex 2 (Scheme 1), whose structure was derived from spectral data, in particular 13C‐NMR.‐data (Table 1). With trimethylamine oxide in benzene, 2 is converted into the urea derivative 3, and yields with cerium (IV) ammonium nitrate the nitrate 4 (Scheme 1). The analogous complexes 6 and 9 have been obtained by irradiation of 1‐phenyl‐vinyl azide (5) and ironpentacarbonyl (Scheme 1) and from vinyl isocyanate (8) and diiron‐enneacarbonyl at 40° (Scheme 2), respectively. The azirine 1, an acetylenic compound and diiron‐enneacarbonyl in benzene react to give complexes of type 10 as the main product (Scheme 3). The structure of complex 10 has been established by X‐ray single crystals analysis. On the 13C‐NMR. time scale the carbonyl groups of compound 10 show a fluxional behaviour: below −50° the CO‐groups of one of the two Fe(CO)3‐groups undergo intranuclear exchange, above −50° the CO‐groups of both Fe(CO)3‐groups undergo intranuclear exchange. Tentative reaction mechanisms for the formation of the complexes of type 2 and 10 are formulated in Schemes 5, 6 and 7.

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Ethenylcarbamic Acid Benzyl Ester and Ethenylcarbamic Acid 1,1-Dimethylethyl Ester

Kamatani

2008

Encyclopedia of Reagents for Organic Synthesis

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Notes- Synthesis of Benzyl Vinylcabamate and 3-O-Vinylcarbamoyl-D-mannitol Pentanitrate

Cited by 13 publications

References 0 publications

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Stickstoffhaltige Dieisen‐hexacarbonyl‐Komplexe aus 3‐Phenyl‐2H‐azirinen

Ethenylcarbamic Acid Benzyl Ester and Ethenylcarbamic Acid 1,1-Dimethylethyl Ester

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Notes- Synthesis of Benzyl Vinylcabamate and 3-O-Vinylcarbamoyl-D-mannitol Pentanitrate

Cited by 13 publications

References 0 publications

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[18F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[18F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Stickstoffhaltige Dieisen‐hexacarbonyl‐Komplexe aus 3‐Phenyl‐2H‐azirinen

Ethenylcarbamic Acid Benzyl Ester and Ethenylcarbamic Acid 1,1-Dimethylethyl Ester

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Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[¹⁸F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo