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SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS

 

作者: Paul E. Gagnon,   Jean L. Boivin,   Jacques Giguere,  

 

期刊: Canadian Journal of Research  (NRC Available online 1950)
卷期: Volume 28b, issue 7  

页码: 352-357

 

ISSN:1923-4287

 

年代: 1950

 

DOI:10.1139/cjr50b-043

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The Darapsky method has been successfully applied to the synthesis of aminoacids from substituted cyanoacetic esters, RCH (CN)COOC2H5. R=CH3CH (CH2)4CH3, CH3CH(CH2)5CH3, CH3(CH2)11, HOCH2CH2,o-ClC6H4CH2,p-CH3C6H4O(CH2)2,p-CH3C6H4O(CH2)3,p-C2H5C6H4O(CH2)2,p-C2H5C6H4O(CH2)3,p-ClC6H4O(CH2)2,p-ClC6H4O(CH2)3,p-BrC6H4O(CH2)3. The esters were prepared by condensation of cyanoacetic ester with suitable bromides. When treated with hydrazine hydrate, they gave rise to hydrazides, which were identified by their anisal derivatives. Azides were obtained by the action of nitrous acid on hydrazides at low temperature and were transformed by heating with alcohol into carbethoxyaminonitriles. Finally, the latter by hydrolysis yielded the following amino acids:dl-α-amino-β-methylcaprylic acid,dl-α-amino-β-methylpelargonic acid,dl-α-aminomyristic acid,dl-α-amino-γ-hydroxybutyric acid,dl-α-amino-γ-p-methylphenoxybutyric acid,dl-α-amino-δ-p-methylphenoxyvaleric acid,dl-α-amino-γ-p-ethylphenoxybutyric acid,dl-α-amino-δ-p-ethylphenoxyvaleric acid,dl-α-amino-γ-p-chlorophenoxybutyric acid,dl-α-amino-δ-p-chlorophenoxyvaleric acid, anddl-α-amino-δ-p-bromophenoxyvaleric acid.

 

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