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The hydrolysis of someN-benzoylamino acids in dilute mineral acid

 

作者: J. B. Capindale,   H. S. Fan,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1967)
卷期: Volume 45, issue 17  

页码: 1921-1924

 

ISSN:0008-4042

 

年代: 1967

 

DOI:10.1139/v67-307

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The behavior ofN-benzoylaspartic acid andN-benzoylglutamic acid has been investigated at 100° in dilute solution in water and aqueous hydrochloric acid within the pH range 3.1–0.5. Some data are presented concerning the hydrolysis of theN-benzoyl derivatives of alanine, β-alanine, leucine, glycine, serine, and β-ethanolamine in water, 0.1 Nhydrochloric acid, and 2 Nhydrochloric acid. Benzoylglutamic acid undergoes a pH-independent conversion into pyrrolid-2-one-5-carboxylic acid, which then hydrolyses in mineral acid to glutamic acid; however,N-benzoylaspartic acid, under similar conditions, hydrolyses much more rapidly by a route which does not involve the corresponding lactam as an intermediate. In anhydrous alcohols the solvolysis ofN-benzoylaspartic acid gives mixtures of aspartic acid and the β ester.First-order rate constants have been obtained for the acid-catalyzed hydrolysis of pyrrolid-2-one-5-carboxylic acid (I) and azetidin-2-one-4-carboxylic acid (II) in water over this pH range.

 

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