A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate
A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the tert -butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford in situ the corresponding...
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| Veröffentlicht in: | Pharmaceutical chemistry journal 2015-03, Vol.48 (12), p.835-839 |
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| container_title | Pharmaceutical chemistry journal |
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| creator | Ratrout, Samer S. Al Sarabi, Ala’eddine M. Sweidan, Kamal A. |
| description | A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the
tert
-butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford
in situ
the corresponding imidazolium methanesulfonate salt which yields zoledronic acid upon reaction with phosphoric acid and phosphorus oxychloride. A possible chemical mechanism for the synthesis of this acid is described. |
| doi_str_mv | 10.1007/s11094-015-1205-0 |
| format | Article |
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tert
-butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford
in situ
the corresponding imidazolium methanesulfonate salt which yields zoledronic acid upon reaction with phosphoric acid and phosphorus oxychloride. A possible chemical mechanism for the synthesis of this acid is described.</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-015-1205-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Acetates ; Bone disorder agents ; Medicine ; Organic Chemistry ; Pharmacology/Toxicology ; Pharmacy ; Phosphates ; Phosphoric acid ; Telomerase</subject><ispartof>Pharmaceutical chemistry journal, 2015-03, Vol.48 (12), p.835-839</ispartof><rights>Springer Science+Business Media New York 2015</rights><rights>COPYRIGHT 2015 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c425t-cff43ccb2513758a236b2512ef0d6bf9b4195281f1213d3c6abf4a8f823ecd273</citedby><cites>FETCH-LOGICAL-c425t-cff43ccb2513758a236b2512ef0d6bf9b4195281f1213d3c6abf4a8f823ecd273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-015-1205-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-015-1205-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Ratrout, Samer S.</creatorcontrib><creatorcontrib>Al Sarabi, Ala’eddine M.</creatorcontrib><creatorcontrib>Sweidan, Kamal A.</creatorcontrib><title>A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the
tert
-butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford
in situ
the corresponding imidazolium methanesulfonate salt which yields zoledronic acid upon reaction with phosphoric acid and phosphorus oxychloride. A possible chemical mechanism for the synthesis of this acid is described.</description><subject>Acetates</subject><subject>Bone disorder agents</subject><subject>Medicine</subject><subject>Organic Chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Phosphates</subject><subject>Phosphoric acid</subject><subject>Telomerase</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kM1KLDEQRoMoOP48gLuA62hV0pmeXjaiV0Hwgl4QNyGdTsZIdyJJXMx9ejOMG0GkFlUJ3ymoQ8gZwgUCtJcZEbqGAUqGHCSDPbJA2QrWgcB9sgDokKGE50NylPMbQKUEXxDT04dg2d9YqA4jvXbOG29DoY-bUF5t9plGR1_iZMcUgze0N36kj0Wn4sOauhRn-mRTYcNH2Uz0bvaj_h8nhqy-emOLLvaEHDg9ZXv61Y_Jv5vrp6tbdv_w5-6qv2em4bIw41wjjBm4RNHKleZiuZ25dTAuB9cNDXaSr9AhRzEKs9SDa_TKrbiwZuStOCbnu71rPVnlg4slaTP7bFTfiEa0LchlTV38kKo12tmbGKzz9f8bgDvApJhzsk69Jz_rtFEIaitf7eSrKl9t5SuoDN8xuWbD2ib1Fj9SqNf_An0C6tiFeA</recordid><startdate>20150301</startdate><enddate>20150301</enddate><creator>Ratrout, Samer S.</creator><creator>Al Sarabi, Ala’eddine M.</creator><creator>Sweidan, Kamal A.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150301</creationdate><title>A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate</title><author>Ratrout, Samer S. ; Al Sarabi, Ala’eddine M. ; Sweidan, Kamal A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c425t-cff43ccb2513758a236b2512ef0d6bf9b4195281f1213d3c6abf4a8f823ecd273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetates</topic><topic>Bone disorder agents</topic><topic>Medicine</topic><topic>Organic Chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Phosphates</topic><topic>Phosphoric acid</topic><topic>Telomerase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ratrout, Samer S.</creatorcontrib><creatorcontrib>Al Sarabi, Ala’eddine M.</creatorcontrib><creatorcontrib>Sweidan, Kamal A.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ratrout, Samer S.</au><au>Al Sarabi, Ala’eddine M.</au><au>Sweidan, Kamal A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2015-03-01</date><risdate>2015</risdate><volume>48</volume><issue>12</issue><spage>835</spage><epage>839</epage><pages>835-839</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the
tert
-butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford
in situ
the corresponding imidazolium methanesulfonate salt which yields zoledronic acid upon reaction with phosphoric acid and phosphorus oxychloride. A possible chemical mechanism for the synthesis of this acid is described.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11094-015-1205-0</doi><tpages>5</tpages></addata></record> |
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| ispartof | Pharmaceutical chemistry journal, 2015-03, Vol.48 (12), p.835-839 |
| issn | 0091-150X 1573-9031 |
| language | eng |
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| source | SpringerLink Journals - AutoHoldings |
| subjects | Acetates Bone disorder agents Medicine Organic Chemistry Pharmacology/Toxicology Pharmacy Phosphates Phosphoric acid Telomerase |
| title | A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate |
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