FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2078379243> ?p ?o ?g. }

• W2078379243 endingPage "M381" @default.
• W2078379243 startingPage "M381" @default.
• W2078379243 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note {6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid by Petra Pádár, Györgyi Kovács and Lajos Kovács * Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary * Author to whom correspondence should be addressed. Molbank 2004, 2004(1), M381; https://doi.org/10.3390/M381 Received: 16 October 2003 / Accepted: 17 March 2004 / Published: 29 March 2004 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes {6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid 2 is one of the substances used in the synthesis of peptide nucleic acid (PNA) adenine monomer and oligomers as well. In our previous work [1] the title acid 2 was prepared by controlled basic hydrolysis of the corresponding N6,N6-dianisoylated ethyl ester derivative. The pH of this reaction solution was carefully maintained to prevent undesired hydrolysis of the N6-(4-methoxybenzoyl) (anisoyl) protecting group which reduced the yield. In our present approach we have chosen the tert-butyl ester 1 as starting material [2] for anisoylation and the resulting N6,N6-dianisoylated substance was subjected to acidic hydrolysis to afford compound 2 in an excellent overall yield. In this latter step the simultaneous removal of one anisoyl and tert-butyl groups happened.Experimental: tert-Butyl (6-amino-9H-purin-9-yl)acetate 1 (10.00 g, 40.1 mmol) [2] was suspended in anhydrous pyridine (120 mL), heated to 80 °C for 30 min, then cooled to room temperature. 4-Methoxybenzoyl chloride (17.90 g, 100 mmol) was added in portions and the mixture was stirred for 18 h at room temperature, then evaporated in vacuo and the residue was coevaporated with toluene (3 x 50 mL). The residue was dissolved in dichloromethane (160 mL) and the solution was washed with 10% (w/v) citric acid (2 x 70 mL), dried (MgSO4) and evaporated in vacuo. The crude product was dissolved in dichloromethane (150 mL), trifluoroacetic acid (32 mL) was added, followed by water (1.6 mL) as a scavenger, and the mixture was stirred for 2 days at room temperature. The solution was evaporated in vacuo, coevaporated with toluene (2 x 50 mL), and acetonitrile (3 x 50 mL). The residue was thoroughly triturated with diethyl ether (5 x 50 mL), and filtered to give a white powder 2 (11.80 g, 90%), mp. 220 °C (darkens), 226 °C (decomp.) TLC: single spot. An analytically pure sample was obtained by recrystallisation from methanol (1500 mL of solvent was required for the above amount).Mp. 231-236 °C. (lit. [3] 222-226 °C).TLC: n-butanol-acetic acid-water: 4:1:1, Rf: 0.37.1H NMR (DMSO-d6, 500 MHz, ppm, asterisks denote interchangeable assignments): 3.84 (s, 3H, OCH3), 5.12 (s, 2H, CH2), 7.07 (d, J=8.3 Hz, 2H, H-3', H-5'), 8.06 (d, J=8.3 Hz, 2H, H-2', H-6'), 8.45 (s, 1H, H-8*), 8.71 (s, 1H, H-2*).13C NMR (DMSO-d6, 125 MHz, ppm, assignment based on decoupled and J-modulated spin echo experiments): 44.18 (CH2), 55.37 (OCH3), 113.59 (C-3', C-5'), 125.00 (C-5), 125.49 (C-1'), 130.44 (C-2', C-6'), 144.84 (C-8), 150.23 (C-4), 151.40 (C-2), 152.39 (C-6), 162.47, 165.00, 168.92 (2xCO, C-4').ESI-MS (m/z): 328 ([M+H]+).Anal. calcd. for C15H13N5O4 (327.295): C, 55.05; H, 4.00; N, 21.40; found: C, 55.23; H, 4.09; N, 21.31%. Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3ReferencesTimár, Z.; Kovács, L.; Kovács, Gy.; Schmél, Z. J. Chem.Soc., Perkin Trans. 1 2000, 19–26.Ceulemans, G.; van Aerschot, A.; Wroblowski, B.; Rozenski, J.; Hendrix, C.; Herdewijn, P. Chem. Eur. J. 1997, 1997–2000.Will, D.W.; Langner, D.; Knolle, J.; Uhlmann, E. Tetrahedron 1995, 51, 12069–12082.Sample availability: sample available from the authors. © 2004 MDPI. All rights reserved. Share and Cite MDPI and ACS Style Pádár, P.; Kovács, G.; Kovács, L. {6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid. Molbank 2004, 2004, M381. https://doi.org/10.3390/M381 AMA Style Pádár P, Kovács G, Kovács L. {6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid. Molbank. 2004; 2004(1):M381. https://doi.org/10.3390/M381 Chicago/Turabian Style Pádár, Petra, Györgyi Kovács, and Lajos Kovács. 2004. {6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid Molbank 2004, no. 1: M381. https://doi.org/10.3390/M381 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
• W2078379243 created "2016-06-24" @default.
• W2078379243 creator A5019115817 @default.
• W2078379243 creator A5028099926 @default.
• W2078379243 creator A5030500200 @default.
• W2078379243 date "2004-03-29" @default.
• W2078379243 modified "2023-10-09" @default.
• W2078379243 title "{6-[(4-Methoxybenzoyl)amino]-9H-purin-9-yl}acetic acid" @default.
• W2078379243 cites W1965828062 @default.
• W2078379243 cites W2017177379 @default.
• W2078379243 cites W2126177981 @default.
• W2078379243 doi "https://doi.org/10.3390/m381" @default.
• W2078379243 hasPublicationYear "2004" @default.
• W2078379243 type Work @default.
• W2078379243 sameAs 2078379243 @default.
• W2078379243 citedByCount "1" @default.
• W2078379243 countsByYear W20783792432022 @default.
• W2078379243 crossrefType "journal-article" @default.
• W2078379243 hasAuthorship W2078379243A5019115817 @default.
• W2078379243 hasAuthorship W2078379243A5028099926 @default.
• W2078379243 hasAuthorship W2078379243A5030500200 @default.
• W2078379243 hasBestOaLocation W20783792431 @default.
• W2078379243 hasConcept C134121241 @default.
• W2078379243 hasConcept C16993767 @default.
• W2078379243 hasConcept C178790620 @default.
• W2078379243 hasConcept C185592680 @default.
• W2078379243 hasConcept C191897082 @default.
• W2078379243 hasConcept C192562407 @default.
• W2078379243 hasConcept C2776673659 @default.
• W2078379243 hasConcept C515207424 @default.
• W2078379243 hasConcept C55493867 @default.
• W2078379243 hasConcept C94412978 @default.
• W2078379243 hasConceptScore W2078379243C134121241 @default.
• W2078379243 hasConceptScore W2078379243C16993767 @default.
• W2078379243 hasConceptScore W2078379243C178790620 @default.
• W2078379243 hasConceptScore W2078379243C185592680 @default.
• W2078379243 hasConceptScore W2078379243C191897082 @default.
• W2078379243 hasConceptScore W2078379243C192562407 @default.
• W2078379243 hasConceptScore W2078379243C2776673659 @default.
• W2078379243 hasConceptScore W2078379243C515207424 @default.
• W2078379243 hasConceptScore W2078379243C55493867 @default.
• W2078379243 hasConceptScore W2078379243C94412978 @default.
• W2078379243 hasIssue "1" @default.
• W2078379243 hasLocation W20783792431 @default.
• W2078379243 hasLocation W20783792432 @default.
• W2078379243 hasOpenAccess W2078379243 @default.
• W2078379243 hasPrimaryLocation W20783792431 @default.
• W2078379243 hasRelatedWork W2003000865 @default.
• W2078379243 hasRelatedWork W2004729465 @default.
• W2078379243 hasRelatedWork W2014383609 @default.
• W2078379243 hasRelatedWork W2092099844 @default.
• W2078379243 hasRelatedWork W2223493887 @default.
• W2078379243 hasRelatedWork W2368632476 @default.
• W2078379243 hasRelatedWork W2370795294 @default.
• W2078379243 hasRelatedWork W2394794149 @default.
• W2078379243 hasRelatedWork W2402688451 @default.
• W2078379243 hasRelatedWork W2991191356 @default.
• W2078379243 hasVolume "2004" @default.
• W2078379243 isParatext "false" @default.
• W2078379243 isRetracted "false" @default.
• W2078379243 magId "2078379243" @default.
• W2078379243 workType "article" @default.