Synthesis of Valsartan via Decarboxylative Biaryl Coupling
An efficient synthesis of the angiotensin II inhibitor valsartan (Diovan) is presented. Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxi...
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| Veröffentlicht in: | Journal of organic chemistry 2007-09, Vol.72 (19), p.7473-7476 |
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| container_title | Journal of organic chemistry |
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| creator | Goossen, Lukas J Melzer, Bettina |
| description | An efficient synthesis of the angiotensin II inhibitor valsartan (Diovan) is presented. Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxide, 1,10-phenanthroline, and palladium(II) bromide, 2-cyanocarboxylic acid was coupled with 1-bromo(4-dimethoxymethyl)benzene in 80% yield and with 4-bromotoluene in 71% yield. The valsartan synthesis using 1-bromo(4-dimethoxymethyl)benzene was completed in four steps overall with a total yield of 39%, via a novel route that presents substantial economical and ecological advantages over the literature process, as it is more concise and stoichiometric amounts of expensive organometallic reagents are avoided. |
| doi_str_mv | 10.1021/jo701391q |
| format | Article |
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Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxide, 1,10-phenanthroline, and palladium(II) bromide, 2-cyanocarboxylic acid was coupled with 1-bromo(4-dimethoxymethyl)benzene in 80% yield and with 4-bromotoluene in 71% yield. The valsartan synthesis using 1-bromo(4-dimethoxymethyl)benzene was completed in four steps overall with a total yield of 39%, via a novel route that presents substantial economical and ecological advantages over the literature process, as it is more concise and stoichiometric amounts of expensive organometallic reagents are avoided.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo701391q</identifier><identifier>PMID: 17715979</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Angiotensin II Type 1 Receptor Blockers - chemical synthesis ; Benzene Derivatives - chemical synthesis ; Benzene Derivatives - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Noncondensed benzenic compounds ; Organic chemistry ; Peptides ; Preparations and properties ; Tetrazoles - chemical synthesis ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ; Valine - analogs & derivatives ; Valine - chemical synthesis ; Valsartan</subject><ispartof>Journal of organic chemistry, 2007-09, Vol.72 (19), p.7473-7476</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-9b5152ca53f752b91b9035bfa662f41a95ccf61fc35c1a4dbb44621d8732709f3</citedby><cites>FETCH-LOGICAL-a447t-9b5152ca53f752b91b9035bfa662f41a95ccf61fc35c1a4dbb44621d8732709f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo701391q$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo701391q$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19081520$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17715979$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Goossen, Lukas J</creatorcontrib><creatorcontrib>Melzer, Bettina</creatorcontrib><title>Synthesis of Valsartan via Decarboxylative Biaryl Coupling</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient synthesis of the angiotensin II inhibitor valsartan (Diovan) is presented. Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxide, 1,10-phenanthroline, and palladium(II) bromide, 2-cyanocarboxylic acid was coupled with 1-bromo(4-dimethoxymethyl)benzene in 80% yield and with 4-bromotoluene in 71% yield. The valsartan synthesis using 1-bromo(4-dimethoxymethyl)benzene was completed in four steps overall with a total yield of 39%, via a novel route that presents substantial economical and ecological advantages over the literature process, as it is more concise and stoichiometric amounts of expensive organometallic reagents are avoided.</description><subject>Angiotensin II Type 1 Receptor Blockers - chemical synthesis</subject><subject>Benzene Derivatives - chemical synthesis</subject><subject>Benzene Derivatives - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Peptides</subject><subject>Preparations and properties</subject><subject>Tetrazoles - chemical synthesis</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Valine - analogs & derivatives</subject><subject>Valine - chemical synthesis</subject><subject>Valsartan</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0DtPwzAUBWALgaA8Bv4AygISQ8DPuGaD8gYJpPIYrRvXBkOatHaC6L_HqBVd8HIHfzo6OgjtEnxEMCXHH43EhCkyXUE9IijOC4X5KuphTGnOaME20GaMHzg9IcQ62iBSEqGk6qGT4axu3230MWtc9gJVhNBCnX15yM6tgVA237MKWv9lszMPYVZlg6abVL5-20ZrLnm7s7hb6Pny4mlwnd8_XN0MTu9z4Fy2uSpF6mRAMCcFLRUpFWaidFAU1HECShjjCuIME4YAH5Ul5wUlo75kVGLl2BY6mOdOQjPtbGz12Edjqwpq23RRF33KFZMswcM5NKGJMVinJ8GPU2dNsP4dSv8NlezeIrQrx3a0lItlEthfAIgGKhegNj4uncL936mTy-fOx9Z-__1D-NSFZFLop8ehVreP_FW9DvXdMhdMTH26UKft_in4A4Guimw</recordid><startdate>20070914</startdate><enddate>20070914</enddate><creator>Goossen, Lukas J</creator><creator>Melzer, Bettina</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070914</creationdate><title>Synthesis of Valsartan via Decarboxylative Biaryl Coupling</title><author>Goossen, Lukas J ; Melzer, Bettina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-9b5152ca53f752b91b9035bfa662f41a95ccf61fc35c1a4dbb44621d8732709f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Angiotensin II Type 1 Receptor Blockers - chemical synthesis</topic><topic>Benzene Derivatives - chemical synthesis</topic><topic>Benzene Derivatives - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Peptides</topic><topic>Preparations and properties</topic><topic>Tetrazoles - chemical synthesis</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Valine - analogs & derivatives</topic><topic>Valine - chemical synthesis</topic><topic>Valsartan</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goossen, Lukas J</creatorcontrib><creatorcontrib>Melzer, Bettina</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goossen, Lukas J</au><au>Melzer, Bettina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Valsartan via Decarboxylative Biaryl Coupling</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-09-14</date><risdate>2007</risdate><volume>72</volume><issue>19</issue><spage>7473</spage><epage>7476</epage><pages>7473-7476</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An efficient synthesis of the angiotensin II inhibitor valsartan (Diovan) is presented. Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxide, 1,10-phenanthroline, and palladium(II) bromide, 2-cyanocarboxylic acid was coupled with 1-bromo(4-dimethoxymethyl)benzene in 80% yield and with 4-bromotoluene in 71% yield. The valsartan synthesis using 1-bromo(4-dimethoxymethyl)benzene was completed in four steps overall with a total yield of 39%, via a novel route that presents substantial economical and ecological advantages over the literature process, as it is more concise and stoichiometric amounts of expensive organometallic reagents are avoided.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17715979</pmid><doi>10.1021/jo701391q</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Angiotensin II Type 1 Receptor Blockers - chemical synthesis Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Noncondensed benzenic compounds Organic chemistry Peptides Preparations and properties Tetrazoles - chemical synthesis Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Valine - analogs & derivatives Valine - chemical synthesis Valsartan |
| title | Synthesis of Valsartan via Decarboxylative Biaryl Coupling |
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