An unconventional method for purifying the N-carboxyanhydride derivatives of γ-alkyl-L-glutamates

Article abstract of DOI:10.1080/00397919908086042

Common impurities in the phosgenation of α-amino acids to produce their N-carboxyanhydride (NCA) derivatives include hydrogen chloride and the hydrochloride salt of the starting amino acid. These impurities can be effectively removed by washing the reaction mixture with water and aqueous bicarbonate at 0 °C prior to isolation of the NCA., despite the well known sensitivity of the NCA to water. The method should be particularly useful for NCA derivatives which are isolated as oils since purifying them by recrystallization or solvent washes is not feasible. This study involved specifically the purification of NCA derivatives from a variety of γ-alkyl- L-glutamates and γ-benzyl-L-glutamate.

Full text of DOI:10.1080/00397919908086042

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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An Unconventional Method
for Purifying the N-
carboxyanhydride Derivatives
of γ-alkyl-L-glutamates
Drew S. Poché a , Michael J. Moore a & Jennifer L.
Bowles a
a Southeastern Louisiana University, Department of
Chemistry and Physics , Hammond, LA, 70402
Published online: 17 Sep 2007.
To cite this article: Drew S. Poché , Michael J. Moore & Jennifer L. Bowles (1999)
An Unconventional Method for Purifying the N-carboxyanhydride Derivatives
of γ-alkyl-L-glutamates, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 29:5, 843-854, DOI:
10.1080/00397919908086042
To link to this article: http://dx.doi.org/10.1080/00397919908086042
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