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SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS

 

作者: Paul E. Gagnon,   Paul A. Boivin,   Hugh M. Craig,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1951)
卷期: Volume 29, issue 1  

页码: 70-75

 

ISSN:0008-4042

 

年代: 1951

 

DOI:10.1139/v51-009

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The Darapsky degradation, by which a carbethoxy group is replaced by an amino group, has been applied successfully to substituted cyanoacetic esters for the preparation of 10 amino acids. The esters were formed by condensation of ethyl cyanoacetate with alkyl or arylalkyl halides. The hydrazides were obtained by treatment of the esters with hydrazine hydrate and identified by their anisal derivatives. Diazotization of the hydrazides gave rise to azides. These were transformed into carbethoxyaminonitriles by refluxing with absolute ethanol. The urethanes, on acid hydrolysis, yielded the amino acids. The following amino acids were synthesized: DL-β-methylleucine, DL-α-amino-β-methylisoheptanoic acid, DL-α-amino-β-cyclohexylpropionic acid, DL-C-o-methylcyclohexylglycine, DL-C-m-methylcyclohexylglycine, DL-C-p-methylcyclohexylglycine, DL-C-o-xylylglycine, DL-C-m-xylylglycine, DL-C-p-xylylglycine, DL-p-ethylalanine.

 

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