Practical synthesis of methyl Z-2-(n-acetylamino) but-2-enoate. An intermediate to D- and L-2-aminobutyric acid

Article abstract of DOI:10.1080/00397919808006866

Treatment of inexpensive L- or DL-threonine methyl ester with acetic anhydride and either pyridine or anhydrous sodium acetate at reflux results in dehydration yielding the N,N-diacetamide of the title compound in >80% yield. Monodeacetylation of the diacetamide with 0.1 equiv of triethylamine in methanol affords the title monoacetamido derivative 1 in nearly quantitative yield.

Full text of DOI:10.1080/00397919808006866

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Synthetic Communications: An
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Practical Synthesis of Methyl
Z-2-(N-Acetylamino) but-2-
Enoate. An Intermediate to D-
and L-2-Aminobutyric Acid
William A. Nugent a & John E. Feaster a
a The DuPont Company Central Research and
Development, P. O. Box 80328, Wilmington, DE,
19880-0328, USA
Version of record first published: 22 Aug 2006.
To cite this article: William A. Nugent & John E. Feaster (1998): Practical Synthesis
of Methyl Z-2-(N-Acetylamino) but-2-Enoate. An Intermediate to D- and L-2-
Aminobutyric Acid, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 28:9, 1617-1623
To link to this article: http://dx.doi.org/10.1080/00397919808006866
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