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Preparation of the Enantiomers of 2-Carbobenzyloxyaminoadipic Acid and Their 1-Benzylesters by M. Claesen; A. Vlietinck; H. Vanderhaeghe is a Chemistry article available to read on EtoBox.

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Different methods of synthesis of 2-aminoadipic acid were examined. The enantiomers of this acid, obtained by enzymatic resolution of the chloroacetylderivative, were transformed into L-and D-2-carbobenzyloxyaminoadipic acids. The two isomers were also prepared by fractional crystallization of the Dand L-threo-1 -p-nitrophenyl-2-amino-I ,3-propanediol salts. The 1 -monobenzylesters of L-, D-, and DL-2-carbobenzyloxyaminoadipic acid were prepared by esterification with phenyldiazomethane. The corresponding ester could also be obtained by reaction of the triethylammonium salt of the acid with benzylbromide in dimethylformamide solution. The structure of the monobenzylester was proved by transformation into the I-benzyl-6-ethylester, from which 2-aminoadipic 6-ethylester was obtained by hydrogenolysis. In a program of synthesis of D-and L-4-carboxy-4-amino-n-butylpenicillin (penicillin N and isopenicillin N), the I-benzylesters of Dand L-2-carbobenzyloxyaniinoadipic acid were needed.

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Author

M. Claesen; A. Vlietinck; H. Vanderhaeghe

Publisher

Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0037-9646)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)