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New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate

Die Herstellung von neuen Phosphonanalogen der Asparagin- und Glutaminsäure in der Reaktion von trivalenten Phosphorchloriden mit Ethyl-acetyloacetat oder Ethyl-lävulinat bzw. Benzylcarbaminat

  • Organische Chemie und Biochemie
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Abstract

Preparation of the phosphonic analogs of α-methylaspartic (4 a–d), glutamic (7 a–b) and α-methylpyroglutamic (5 a–b) acids by aminoalkylation of trivalent phosphorus chlorides with ethyl esters of oxoalkyloacids and benzyl carbamate is described. The phosphonic analogs of pyroglutamic acid (8 a–b) was obtained by the cyclization of the corresponding esters (9 a–b). The stability of the phosphonic analogs of pyroglutamic acid in acidic and alkaline media was also studied.

Zusammenfassung

Es wurde die Darstellung der Phosphonanalogen der α-Methylasparaginsäure (4 a–d), Glutamin- (7 a–b) und α-Methylpyroglutaminsäure (5 a–b) in der Reaktion der trivalenten Phosphorchloride und der Oxoalkansäureethylester sowie des Benzylcarbaminats beschrieben. In der Ringschlußreaktion der Ester (9 a–b) erhält man Phosphonanaloge der Pyroglutaminsäure. Die Stabilität der Analogen der Pyroglutaminsäure wurde in sauren und alkalischen Medien geprüft.

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Authors and Affiliations

  1. Institute of Organic and Physical Chemistry, Technical University (Politechnika) of Wrocław, PL-50-370, Wrocław, Poland

    Józef Oleksyszyn, Ewa Gruszecka, Paweł Kafarski & Przemysław Mastalerz

Authors
  1. Józef Oleksyszyn
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  2. Ewa Gruszecka
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  3. Paweł Kafarski
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  4. Przemysław Mastalerz
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Oleksyszyn, J., Gruszecka, E., Kafarski, P. et al. New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate. Monatsh Chem 113, 59–71 (1982). https://doi.org/10.1007/BF00814338

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  • DOI: https://doi.org/10.1007/BF00814338

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