A detailed mechanistic investigation into the reaction of 3-methylpentanoic acid with Meldrum's acid utilizing online NMR spectroscopy
A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. This study is an expansion of a previous analysis of this chemical transformation in the synthesis of an active pharmaceutical ingredient imagabali...
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| Veröffentlicht in: | Magnetic resonance in chemistry 2016-06, Vol.54 (6), p.477-484 |
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| container_title | Magnetic resonance in chemistry |
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| creator | Dunn, Anna L. Codina, Anna Foley, David A. Marquez, Brian L. Zell, Mark T. |
| description | A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. This study is an expansion of a previous analysis of this chemical transformation in the synthesis of an active pharmaceutical ingredient imagabalin. The 3‐methylpentanoic acid analogue reveals similar behavior under the reaction conditions. Online NMR spectroscopy and offline characterization experiments reveal new information about the mechanism, providing conclusive spectroscopic evidence for the previously hypothesized dimer anhydride intermediate species 3‐methylpentanoic anhydride as a productive intermediate. The presence of an acyl chloride intermediate species, 3‐methylpentanoyl chloride, is also revealed for the first time in this synthesis. Copyright © 2015 John Wiley & Sons, Ltd.
A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. Structural characterization of a number of reaction species is presented, providing evidence of the productive intermediates to product formation. |
| doi_str_mv | 10.1002/mrc.4317 |
| format | Article |
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A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. Structural characterization of a number of reaction species is presented, providing evidence of the productive intermediates to product formation.</description><identifier>ISSN: 0749-1581</identifier><identifier>EISSN: 1097-458X</identifier><identifier>DOI: 10.1002/mrc.4317</identifier><identifier>PMID: 26332370</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>Anhydrides ; Chlorides ; Dimers ; NMR reaction monitoring ; NMR spectroscopy ; Online ; online NMR spectroscopy ; reaction mechanism ; Structural analysis ; Synthesis ; Transformations</subject><ispartof>Magnetic resonance in chemistry, 2016-06, Vol.54 (6), p.477-484</ispartof><rights>Copyright © 2015 John Wiley & Sons, Ltd.</rights><rights>Copyright © 2016 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4207-744b1000392b095001d5c5add2fa03a62cf5e0b48abe967683f26d7dad62ba503</citedby><cites>FETCH-LOGICAL-c4207-744b1000392b095001d5c5add2fa03a62cf5e0b48abe967683f26d7dad62ba503</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmrc.4317$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmrc.4317$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26332370$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dunn, Anna L.</creatorcontrib><creatorcontrib>Codina, Anna</creatorcontrib><creatorcontrib>Foley, David A.</creatorcontrib><creatorcontrib>Marquez, Brian L.</creatorcontrib><creatorcontrib>Zell, Mark T.</creatorcontrib><title>A detailed mechanistic investigation into the reaction of 3-methylpentanoic acid with Meldrum's acid utilizing online NMR spectroscopy</title><title>Magnetic resonance in chemistry</title><addtitle>Magn. Reson. Chem</addtitle><description>A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. This study is an expansion of a previous analysis of this chemical transformation in the synthesis of an active pharmaceutical ingredient imagabalin. The 3‐methylpentanoic acid analogue reveals similar behavior under the reaction conditions. Online NMR spectroscopy and offline characterization experiments reveal new information about the mechanism, providing conclusive spectroscopic evidence for the previously hypothesized dimer anhydride intermediate species 3‐methylpentanoic anhydride as a productive intermediate. The presence of an acyl chloride intermediate species, 3‐methylpentanoyl chloride, is also revealed for the first time in this synthesis. Copyright © 2015 John Wiley & Sons, Ltd.
A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. Structural characterization of a number of reaction species is presented, providing evidence of the productive intermediates to product formation.</description><subject>Anhydrides</subject><subject>Chlorides</subject><subject>Dimers</subject><subject>NMR reaction monitoring</subject><subject>NMR spectroscopy</subject><subject>Online</subject><subject>online NMR spectroscopy</subject><subject>reaction mechanism</subject><subject>Structural analysis</subject><subject>Synthesis</subject><subject>Transformations</subject><issn>0749-1581</issn><issn>1097-458X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkdtuFCEAhonR2G018QkMiRf2ZiqHYRgum422mm5Nmpp6RxhgutQZmAJjXR_A55a6a01MTLzikI8ffj4AXmB0hBEib8aoj2qK-SOwwEjwqmbt58dggXgtKsxavAf2U7pBCAnB6VOwRxpKCeVoAX4cQ2OzcoM1cLR6rbxL2Wno_FdbJtcqu-DLKgeY1xZGq_SvndBDWo02rzfDZH1WPpRDSjsD71xew5UdTJzH12m7N2c3uO_OX8PgB-ctPF9dwDRZnWNIOkybZ-BJr4Zkn-_GA_Dp3dvL5Wl19vHk_fL4rNI1Qbzidd2VwogK0iHBEMKGaaaMIb1CVDVE98yirm5VZ0XDm5b2pDHcKNOQTjFED8DhNneK4XYuDeXokrbDoLwNc5K4xQ3i5cf-A-Wi3C8Y4wV99Rd6E-boS5FCtYJiygj5E6hL6RRtL6foRhU3EiN5r1EWjfJeY0Ff7gLnbrTmAfztrQDVFrgr5jb_DJKri-UucMcXu_bbA6_iF9lwypm8Oj-Rp5flpZheyQ_0J5r8tcM</recordid><startdate>201606</startdate><enddate>201606</enddate><creator>Dunn, Anna L.</creator><creator>Codina, Anna</creator><creator>Foley, David A.</creator><creator>Marquez, Brian L.</creator><creator>Zell, Mark T.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201606</creationdate><title>A detailed mechanistic investigation into the reaction of 3-methylpentanoic acid with Meldrum's acid utilizing online NMR spectroscopy</title><author>Dunn, Anna L. ; Codina, Anna ; Foley, David A. ; Marquez, Brian L. ; Zell, Mark T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4207-744b1000392b095001d5c5add2fa03a62cf5e0b48abe967683f26d7dad62ba503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Anhydrides</topic><topic>Chlorides</topic><topic>Dimers</topic><topic>NMR reaction monitoring</topic><topic>NMR spectroscopy</topic><topic>Online</topic><topic>online NMR spectroscopy</topic><topic>reaction mechanism</topic><topic>Structural analysis</topic><topic>Synthesis</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dunn, Anna L.</creatorcontrib><creatorcontrib>Codina, Anna</creatorcontrib><creatorcontrib>Foley, David A.</creatorcontrib><creatorcontrib>Marquez, Brian L.</creatorcontrib><creatorcontrib>Zell, Mark T.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Magnetic resonance in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dunn, Anna L.</au><au>Codina, Anna</au><au>Foley, David A.</au><au>Marquez, Brian L.</au><au>Zell, Mark T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A detailed mechanistic investigation into the reaction of 3-methylpentanoic acid with Meldrum's acid utilizing online NMR spectroscopy</atitle><jtitle>Magnetic resonance in chemistry</jtitle><addtitle>Magn. Reson. Chem</addtitle><date>2016-06</date><risdate>2016</risdate><volume>54</volume><issue>6</issue><spage>477</spage><epage>484</epage><pages>477-484</pages><issn>0749-1581</issn><eissn>1097-458X</eissn><abstract>A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. This study is an expansion of a previous analysis of this chemical transformation in the synthesis of an active pharmaceutical ingredient imagabalin. The 3‐methylpentanoic acid analogue reveals similar behavior under the reaction conditions. Online NMR spectroscopy and offline characterization experiments reveal new information about the mechanism, providing conclusive spectroscopic evidence for the previously hypothesized dimer anhydride intermediate species 3‐methylpentanoic anhydride as a productive intermediate. The presence of an acyl chloride intermediate species, 3‐methylpentanoyl chloride, is also revealed for the first time in this synthesis. Copyright © 2015 John Wiley & Sons, Ltd.
A thorough investigation into the mechanism of the reaction of 3‐methylpentanoic acid and Meldrum's acid using online NMR spectroscopy is reported. Structural characterization of a number of reaction species is presented, providing evidence of the productive intermediates to product formation.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>26332370</pmid><doi>10.1002/mrc.4317</doi><tpages>8</tpages></addata></record> |
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| ispartof | Magnetic resonance in chemistry, 2016-06, Vol.54 (6), p.477-484 |
| issn | 0749-1581 1097-458X |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Anhydrides Chlorides Dimers NMR reaction monitoring NMR spectroscopy Online online NMR spectroscopy reaction mechanism Structural analysis Synthesis Transformations |
| title | A detailed mechanistic investigation into the reaction of 3-methylpentanoic acid with Meldrum's acid utilizing online NMR spectroscopy |
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