NEW TYPE OF DERIVATIZATION REAGENTS FOR LIQUID CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERIC HYDROXYL COMPOUNDS

Two sensitive chiral derivatization reagents, (+)- and (-)-2-methyl-1, 1'-binaphthalene-2'-carbonyl nitriles, have been newly developed. These were prepared from dimethyl 1, 1'-binaphthalene-2, 2'-dicarboxylate in several steps. Enantiomeric alcohols were readily condensed with t...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 30; no. 12; pp. 4597 - 4599
Main Authors Nambara, Toshio, Goto, Nobuharu, Goto, Junichi
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 01.01.1982
公益社団法人日本薬学会
Subjects
acyl nitrile
chiral axis compound
chiral derivatization reagent
diastereomeric ester
fluorescence labeling
high-performance liquid chromatography
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ISSN0009-2363
1347-5223
1347-5223
DOI10.1248/cpb.30.4597

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Summary:Two sensitive chiral derivatization reagents, (+)- and (-)-2-methyl-1, 1'-binaphthalene-2'-carbonyl nitriles, have been newly developed. These were prepared from dimethyl 1, 1'-binaphthalene-2, 2'-dicarboxylate in several steps. Enantiomeric alcohols were readily condensed with the chiral reagent in the presence of triethylamine under mild conditions. The diastereomeric esters formed from enantiomeric hydroxy acids were efficiently resolved by high-performance liquid chromatography on a normal phase column with n-pentane/ethyl acetate. These were highly responsive to a fluorescence detector (excitation wavelength 342 nm ; emission wavelength 420 nm) with a detection limit of 200 pg.
ISSN:0009-2363
1347-5223
1347-5223
DOI:10.1248/cpb.30.4597