An Improved Synthesis of t-Butyl N-(4-propargylaminobenzoyl)-γ-oligo (L-glutamate )s

A simple synthesis in solution, of the series of six consecutive t-butyl N-(4-propargylaminobenzoyl)-yoligo( L-glutamate)s (8-13) containing from two to seven L-glutamic acid residues (Scheme 1) is described. a-t-Butyl N-(4-propargylaminobenzoyl)-L-glutamate (1), the versatile synthon is coupled wit...

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Bibliographic Details
Published in:Pteridines 1995-05, Vol.6 (2), p.41-44
Main Authors: Kempny, Michal, Rzeszotarska, Barbara, Pawelczak, Krzysztof
Format: Article
Language:English
Subjects:
2-chloroI- methylpyridinium tosylate
HPLC
N°-Propargyl antifolates
t-Butyl N-(4 propargylaminobenzoyl)-y-oligo(L-glutamate)s
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Summary:A simple synthesis in solution, of the series of six consecutive t-butyl N-(4-propargylaminobenzoyl)-yoligo( L-glutamate)s (8-13) containing from two to seven L-glutamic acid residues (Scheme 1) is described. a-t-Butyl N-(4-propargylaminobenzoyl)-L-glutamate (1), the versatile synthon is coupled with one of the t-butyl y-oligo(L-glutamate)s (2-7) by means of 2-chloro-l-methylpyridinium tosylate to give the title compounds in 91-95% yield subsequent to edulcoration of a post-reaction mixture and crystallization. These compounds were characterized by melting points, elemental analyses and HPLC and are 96.7-100.0% pure according to the last method (Table I).
ISSN:0933-4807
2195-4720
DOI:10.1515/pteridines.1995.6.2.41