1-(4-Aminobenzoyl)piperidine-4-carbamic acid tert-butyl ester - CAS 883106-38-5
Catalog number: 883106-38-5
Category: Main Product
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[1-(4-AMINO-BENZOYL)-PIPERIDIN-4-YL]-CARBAMIC ACID TERT-BUTYL ESTER; 1-(4-Aminobenzoyl)piperidine-4-carbamic acid tert-butyl ester
1.Synthesis and biological activity of the 2-desamino and 2-desamino-2-methyl analogues of aminopterin and methotrexate.
Rosowsky A1, Forsch RA, Moran RG, Freisheim JH. J Med Chem. 1991 Jan;34(1):227-34.
The previously undescribed 2-desamino and 2-desamino-2-methyl analogues of aminopterin (AMT) and methotrexate (MTX) were synthesized from 2-amino-5-(chloromethyl)pyrazine-3-carbonitrile. The AMT analogues were obtained via a three-step sequence consisting of condensation with di-tert-butyl N-(4-aminobenzoyl)-L-glutamate, heating with formamidine or acetamidine acetate, and mild acidolysis with trifluoroacetic acid. The MTX analogues were prepared similarly, except that 2-amino-5-(chloromethyl)pyrazine-3-carbonitrile was condensed with 4-(N-methylamino)benzoic acid and the resulting product was annulated with formamidine or acetamidine acetate to obtain the 2-desamino and 2-desamino-2-methyl analogues, respectively, of 4-amino-4-deoxy-N10-methylpteroic acid. Condensation with di-tert-butyl L-glutamate in the presence of diethyl phosphorocyanidate followed by ester cleavage with trifluoroacetic acid was then carried out. Retention of the L configuration in the glutamate moiety during this synthesis was demonstrated by rapid and essentially complete hydrolysis with carboxypeptidase G1 under conditions that likewise cleaved the L enantiomer of MTX but left the D enantiomer unaffected.
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CAS 883106-38-5 1-(4-Aminobenzoyl)piperidine-4-carbamic acid tert-butyl ester

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