Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine
Both E and Z "cyclopropylogs" of DL-phenylalanine ( Delta super(E)-Phe and Delta super(Z)-Phe) have been prepared by the cyclopropanation of each 4-benzylidene-2-phenyl-5(4H)-oxazolone isomer with diazomethane to form the three-membered ring. Opening of the oxazoline ring to give the benzy...
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| Veröffentlicht in: | Journal of organic chemistry 1982-08, Vol.47 (17), p.3270-3273 |
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| container_issue | 17 |
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| container_title | Journal of organic chemistry |
| container_volume | 47 |
| creator | King, Stephen W Riordan, James M Holt, Elizabeth M Stammer, Charles H |
| description | Both E and Z "cyclopropylogs" of DL-phenylalanine ( Delta super(E)-Phe and Delta super(Z)-Phe) have been prepared by the cyclopropanation of each 4-benzylidene-2-phenyl-5(4H)-oxazolone isomer with diazomethane to form the three-membered ring. Opening of the oxazoline ring to give the benzyl ester followed by debenzoylation using Meerwein's reagent gave the benzyl ester hydrochloride of DL- Delta super(Z)-Phe. Hydrogenation gave the free amino acid in good yield. Isomerization of the (Z)-oxazolone to the E isomer followed by cyclopropanation and methyl ester formation gave N-Bz-DL- Delta super(E)-PheOMe. Debenzoylation and conversion to the N-Boc methyl ester followed. Saponification of the ester followed by Boc removal (HCl) gave DL- Delta super(E)-Phe hydrochloride in good yield. |
| doi_str_mv | 10.1021/jo00138a014 |
| format | Article |
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Opening of the oxazoline ring to give the benzyl ester followed by debenzoylation using Meerwein's reagent gave the benzyl ester hydrochloride of DL- Delta super(Z)-Phe. Hydrogenation gave the free amino acid in good yield. Isomerization of the (Z)-oxazolone to the E isomer followed by cyclopropanation and methyl ester formation gave N-Bz-DL- Delta super(E)-PheOMe. Debenzoylation and conversion to the N-Boc methyl ester followed. Saponification of the ester followed by Boc removal (HCl) gave DL- Delta super(E)-Phe hydrochloride in good yield.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00138a014</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>cyclopropylphenylalanine</subject><ispartof>Journal of organic chemistry, 1982-08, Vol.47 (17), p.3270-3273</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a398t-7edb1429597129e13f4c8967c096533a46212820ae56a7a6d8ab7b45d05f737e3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo00138a014$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo00138a014$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids></links><search><creatorcontrib>King, Stephen W</creatorcontrib><creatorcontrib>Riordan, James M</creatorcontrib><creatorcontrib>Holt, Elizabeth M</creatorcontrib><creatorcontrib>Stammer, Charles H</creatorcontrib><title>Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Both E and Z "cyclopropylogs" of DL-phenylalanine ( Delta super(E)-Phe and Delta super(Z)-Phe) have been prepared by the cyclopropanation of each 4-benzylidene-2-phenyl-5(4H)-oxazolone isomer with diazomethane to form the three-membered ring. Opening of the oxazoline ring to give the benzyl ester followed by debenzoylation using Meerwein's reagent gave the benzyl ester hydrochloride of DL- Delta super(Z)-Phe. Hydrogenation gave the free amino acid in good yield. Isomerization of the (Z)-oxazolone to the E isomer followed by cyclopropanation and methyl ester formation gave N-Bz-DL- Delta super(E)-PheOMe. Debenzoylation and conversion to the N-Boc methyl ester followed. Saponification of the ester followed by Boc removal (HCl) gave DL- Delta super(E)-Phe hydrochloride in good yield.</description><subject>cyclopropylphenylalanine</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><recordid>eNptkE1Lw0AQhhdRsFZP_oGctEVW9yO7SbxJqVaoH9B68bJMNhuamo-6m0Lz712JFAXnMnN43nfeGYTOKbmmhNGbdUMI5TEQGh6gARWMYJmQ8BANCGEMcyb5MTpxbk18CSEGqF10dbsyrnBBkwcWtKkKHYymYxxAnQWj9zGmGKqibjDDm5Wpu1J3umw2ttlAbTTYtNl1pdeALrLbv8o92ZW9FEqoi9qcoqMcSmfOfvoQvd1Pl5MZnr88PE7u5hh4Erc4MllKQ5aIJKIsMZTnoY4TGWmSSME5hJJRFjMCRkiIQGYxpFEaioyIPOKR4UN00fv6DJ9b41pVFU6b0qcwzdYpyoVgnDEPXvWgto1z1uRqY4sKbKcoUd-fVb8-62nc04VrzW6Pgv1Q0u8Vavm6ULMwXj6Hfnjy_GXPg3beaGtrf_S_zl8arIVV</recordid><startdate>198208</startdate><enddate>198208</enddate><creator>King, Stephen W</creator><creator>Riordan, James M</creator><creator>Holt, Elizabeth M</creator><creator>Stammer, Charles H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>198208</creationdate><title>Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine</title><author>King, Stephen W ; Riordan, James M ; Holt, Elizabeth M ; Stammer, Charles H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a398t-7edb1429597129e13f4c8967c096533a46212820ae56a7a6d8ab7b45d05f737e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><topic>cyclopropylphenylalanine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>King, Stephen W</creatorcontrib><creatorcontrib>Riordan, James M</creatorcontrib><creatorcontrib>Holt, Elizabeth M</creatorcontrib><creatorcontrib>Stammer, Charles H</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>King, Stephen W</au><au>Riordan, James M</au><au>Holt, Elizabeth M</au><au>Stammer, Charles H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1982-08</date><risdate>1982</risdate><volume>47</volume><issue>17</issue><spage>3270</spage><epage>3273</epage><pages>3270-3273</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Both E and Z "cyclopropylogs" of DL-phenylalanine ( Delta super(E)-Phe and Delta super(Z)-Phe) have been prepared by the cyclopropanation of each 4-benzylidene-2-phenyl-5(4H)-oxazolone isomer with diazomethane to form the three-membered ring. Opening of the oxazoline ring to give the benzyl ester followed by debenzoylation using Meerwein's reagent gave the benzyl ester hydrochloride of DL- Delta super(Z)-Phe. Hydrogenation gave the free amino acid in good yield. Isomerization of the (Z)-oxazolone to the E isomer followed by cyclopropanation and methyl ester formation gave N-Bz-DL- Delta super(E)-PheOMe. Debenzoylation and conversion to the N-Boc methyl ester followed. Saponification of the ester followed by Boc removal (HCl) gave DL- Delta super(E)-Phe hydrochloride in good yield.</abstract><pub>American Chemical Society</pub><doi>10.1021/jo00138a014</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 1982-08, Vol.47 (17), p.3270-3273 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_13552322 |
| source | ACS Publications |
| subjects | cyclopropylphenylalanine |
| title | Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine |
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