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1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties
The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) - sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetyla...
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| Published in: | Amino acids 2007-11, Vol.33 (4), p.663-667 |
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| cites | cdi_FETCH-LOGICAL-c384t-7ebf09ee1d24e3fd84e91898072c4e1f17f9bb2b66467470ca30a090524628843 |
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| container_title | Amino acids |
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| creator | Kudzin, Z. H Depczyński, R Kudzin, M. H Łuczak, J Drabowicz, J |
| description | The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) - sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetylation of 1-aminoalkylphosphonic acids (AAP) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AAP + TFAA/TFA[rightward arrow]2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2[rightward arrow]TFA-AAP). These intermediates 2 presented mixtures of the type of mixed anhydrides of TFAA and 1-(N-trifluoroacetylamino)alkylphosphonic, pyrophosphonic and polyphosphonic acids, which underwent rapid and quantitative conversion to corresponding TFA-AAP during treatment with an excess of water. The title acids were isolated by direct evaporation of the corresponding post-reaction mixtures, and their physicochemical proprieties, including deacylation abilities, were determined. TFA-AAP compounds can be re-converted into the starting amino acids AAP under respectively mild conditions (AAP[rightward arrow]TFA-AAP[rightward arrow]AAP). |
| doi_str_mv | 10.1007/s00726-006-0472-1 |
| format | article |
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H ; Depczyński, R ; Kudzin, M. H ; Łuczak, J ; Drabowicz, J</creator><creatorcontrib>Kudzin, Z. H ; Depczyński, R ; Kudzin, M. H ; Łuczak, J ; Drabowicz, J</creatorcontrib><description>The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) - sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetylation of 1-aminoalkylphosphonic acids (AAP) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AAP + TFAA/TFA[rightward arrow]2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2[rightward arrow]TFA-AAP). These intermediates 2 presented mixtures of the type of mixed anhydrides of TFAA and 1-(N-trifluoroacetylamino)alkylphosphonic, pyrophosphonic and polyphosphonic acids, which underwent rapid and quantitative conversion to corresponding TFA-AAP during treatment with an excess of water. The title acids were isolated by direct evaporation of the corresponding post-reaction mixtures, and their physicochemical proprieties, including deacylation abilities, were determined. TFA-AAP compounds can be re-converted into the starting amino acids AAP under respectively mild conditions (AAP[rightward arrow]TFA-AAP[rightward arrow]AAP).</description><identifier>ISSN: 0939-4451</identifier><identifier>EISSN: 1438-2199</identifier><identifier>DOI: 10.1007/s00726-006-0472-1</identifier><identifier>PMID: 17146591</identifier><language>eng</language><publisher>Austria: Vienna : Springer-Verlag</publisher><subject>1-(N- Trifluoroacetylamino)alkylphosphonic acids ; 1-Aminoalkylphosphonic acids ; Acetylation ; Acylation ; Amino acids ; Aminophosphonic acids ; Anhydrides ; Conversion ; Evaporation ; Hydrolysis ; Magnetic Resonance Spectroscopy ; Mixed anhydrides ; Molecular Structure ; Organophosphonates - chemical synthesis ; Organophosphonates - chemistry ; Synthesis ; Transformations ; Trifluoroacetylation</subject><ispartof>Amino acids, 2007-11, Vol.33 (4), p.663-667</ispartof><rights>Springer-Verlag 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-7ebf09ee1d24e3fd84e91898072c4e1f17f9bb2b66467470ca30a090524628843</citedby><cites>FETCH-LOGICAL-c384t-7ebf09ee1d24e3fd84e91898072c4e1f17f9bb2b66467470ca30a090524628843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17146591$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kudzin, Z. H</creatorcontrib><creatorcontrib>Depczyński, R</creatorcontrib><creatorcontrib>Kudzin, M. H</creatorcontrib><creatorcontrib>Łuczak, J</creatorcontrib><creatorcontrib>Drabowicz, J</creatorcontrib><title>1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties</title><title>Amino acids</title><addtitle>Amino Acids</addtitle><description>The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) - sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetylation of 1-aminoalkylphosphonic acids (AAP) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AAP + TFAA/TFA[rightward arrow]2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2[rightward arrow]TFA-AAP). These intermediates 2 presented mixtures of the type of mixed anhydrides of TFAA and 1-(N-trifluoroacetylamino)alkylphosphonic, pyrophosphonic and polyphosphonic acids, which underwent rapid and quantitative conversion to corresponding TFA-AAP during treatment with an excess of water. The title acids were isolated by direct evaporation of the corresponding post-reaction mixtures, and their physicochemical proprieties, including deacylation abilities, were determined. TFA-AAP compounds can be re-converted into the starting amino acids AAP under respectively mild conditions (AAP[rightward arrow]TFA-AAP[rightward arrow]AAP).</description><subject>1-(N- Trifluoroacetylamino)alkylphosphonic acids</subject><subject>1-Aminoalkylphosphonic acids</subject><subject>Acetylation</subject><subject>Acylation</subject><subject>Amino acids</subject><subject>Aminophosphonic acids</subject><subject>Anhydrides</subject><subject>Conversion</subject><subject>Evaporation</subject><subject>Hydrolysis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mixed anhydrides</subject><subject>Molecular Structure</subject><subject>Organophosphonates - chemical synthesis</subject><subject>Organophosphonates - chemistry</subject><subject>Synthesis</subject><subject>Transformations</subject><subject>Trifluoroacetylation</subject><issn>0939-4451</issn><issn>1438-2199</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNp90T1PHDEQBmALBcGF5AekSU5CiqBwMuNv0yFEAhIiRaC2vLveYLK3Puzd4v49Pt1JSClSzLh5ZqzRS8gnhG8IoL-X2piiALWEZhQPyAIFN5Shte_IAiy3VAiJx-R9Kc8AyAyqI3KMGoWSFhfkFunZPX3IsR_mlJNvw7QZ_CqO6dwPfzfD-imVWmNsl76NXblYls04PYUSy9KP3XKd0zrkKYbygRz2fijh4_49IY8_rh-ubujdr5-3V5d3tOVGTFSHpgcbAnZMBN53RgSLxpp6SSsC9qh72zSsUUooLTS0noMHC5IJxYwR_IR83e2tX7_MoUxuFUsbhsGPIc3FKSMrV7zCs_9CBLRKS2m29PQf-pzmPNYzqrJSg7RGVYU71eZUSg69W-e48nlTkdsG4naBuBqI2wbisM583m-em1Xo3ib2CVTwZQd6n5z_k2Nxj78ZIAcwTDOp-SvwkI2a</recordid><startdate>20071101</startdate><enddate>20071101</enddate><creator>Kudzin, Z. 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H ; Depczyński, R ; Kudzin, M. H ; Łuczak, J ; Drabowicz, J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-7ebf09ee1d24e3fd84e91898072c4e1f17f9bb2b66467470ca30a090524628843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>1-(N- Trifluoroacetylamino)alkylphosphonic acids</topic><topic>1-Aminoalkylphosphonic acids</topic><topic>Acetylation</topic><topic>Acylation</topic><topic>Amino acids</topic><topic>Aminophosphonic acids</topic><topic>Anhydrides</topic><topic>Conversion</topic><topic>Evaporation</topic><topic>Hydrolysis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mixed anhydrides</topic><topic>Molecular Structure</topic><topic>Organophosphonates - chemical synthesis</topic><topic>Organophosphonates - chemistry</topic><topic>Synthesis</topic><topic>Transformations</topic><topic>Trifluoroacetylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kudzin, Z. 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H</au><au>Depczyński, R</au><au>Kudzin, M. H</au><au>Łuczak, J</au><au>Drabowicz, J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties</atitle><jtitle>Amino acids</jtitle><addtitle>Amino Acids</addtitle><date>2007-11-01</date><risdate>2007</risdate><volume>33</volume><issue>4</issue><spage>663</spage><epage>667</epage><pages>663-667</pages><issn>0939-4451</issn><eissn>1438-2199</eissn><abstract>The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) - sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetylation of 1-aminoalkylphosphonic acids (AAP) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AAP + TFAA/TFA[rightward arrow]2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2[rightward arrow]TFA-AAP). These intermediates 2 presented mixtures of the type of mixed anhydrides of TFAA and 1-(N-trifluoroacetylamino)alkylphosphonic, pyrophosphonic and polyphosphonic acids, which underwent rapid and quantitative conversion to corresponding TFA-AAP during treatment with an excess of water. The title acids were isolated by direct evaporation of the corresponding post-reaction mixtures, and their physicochemical proprieties, including deacylation abilities, were determined. TFA-AAP compounds can be re-converted into the starting amino acids AAP under respectively mild conditions (AAP[rightward arrow]TFA-AAP[rightward arrow]AAP).</abstract><cop>Austria</cop><pub>Vienna : Springer-Verlag</pub><pmid>17146591</pmid><doi>10.1007/s00726-006-0472-1</doi><tpages>5</tpages></addata></record> |
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| ispartof | Amino acids, 2007-11, Vol.33 (4), p.663-667 |
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| subjects | 1-(N- Trifluoroacetylamino)alkylphosphonic acids 1-Aminoalkylphosphonic acids Acetylation Acylation Amino acids Aminophosphonic acids Anhydrides Conversion Evaporation Hydrolysis Magnetic Resonance Spectroscopy Mixed anhydrides Molecular Structure Organophosphonates - chemical synthesis Organophosphonates - chemistry Synthesis Transformations Trifluoroacetylation |
| title | 1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties |
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