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Computer-assisted automated synthesis. III. Synthesis of substituted N-(carboxyalkyl) amino-acid tert-butyl ester derivatives.
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MedLine Citation:
PMID:  18924904     Owner:  NLM     Status:  In-Data-Review    
A versatile automated synthesis apparatus, equipped with a chemical artificial intelligence, was developed to prepare and isolate a wide variety of compounds. The apparatus was to the synthesis of substituted N-(carboxyalkyl)amino-acids. The apparatus [1,2] is composed of units for performing various tasks,for example reagent supply, reaction, purification and separation, each linked to a control system. All synthetic processes, including washing and drying of the apparatus after each synthetic run, were automatically performed from the mixing of the reactants to the isolation of the products as powders or crystals. The reaction of an amino-acid tertbutyl ester acetic acid salt with a 2-keto acid sodium salt produces an unstable intermediate, Schiff base, which is reduced with sodum cyanoborohydride to give a substituted N-(carboxyalkyl)aminoacid tert-butyl ester sodium salt. The equilibrium and the consecutive reactions were controlled by adding sodium cyanoborohydride using the artificial intelligence software, which contained novel kinetic equations [3] and substituent effects [4].Substitued N-(carboxyalkyl)amino-acid tert-butyl esters, 90 derivatives, were automatically synthesized using the computerassisted automated synthesis apparatus. The syntheses were performed unattended 24 hours a day, except for supplying the raw materials, reagents and solvents. The apparatus is extremely valuable for synthesizing many derivatives of a particular compound. The configurations of the products were determined by circular dichroism measurements.
N Hayashi; T Sugawara; S Kato
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of automatic chemistry     Volume:  13     ISSN:  0142-0453     ISO Abbreviation:  J Automat Chem     Publication Date:  1991  
Date Detail:
Created Date:  2008-10-17     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8209386     Medline TA:  J Automat Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  187-97     Citation Subset:  -    
Chemistry Research Laboratories Research and Development Division Takeda Chemical Industries Ltd Juso Honmachi 2- chome, Yodogawaku Osaka 532 Japan.
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Journal Information
Journal ID (nlm-ta): J Automat Chem
ISSN: 0142-0453
Publisher: Hindawi Publishing Corporation
Article Information
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Copyright ? 1991 Hindawi Publishing Corporation.
open-access: This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Print publication date: Year: 1991
Volume: 13 Issue: 5
First Page: 187 Last Page: 197
ID: 2547931
PubMed Id: 18924904
Publisher Item Identifier: S1463924691000330
DOI: 10.1155/S1463924691000330

Computer-assisted automated synthesis. III. Synthesis of substituted N-(carboxyalkyl) amino-acid tert-butyl ester derivatives
Nobuyoshi Hayashi
Tohru Sugawara
Shinji Kato
Chemistry Research LaboratoriesResearch and Development DivisionTakeda Chemical Industries LtdJuso Honmachi 2- chome, YodogawakuOsaka532Japan

Article Categories:
  • Research Article

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