NOVEL CHIRAL DERIVATIZING AGENTS FOR 1H NMR DETERMINATION OF ENANTIOMERIC PURITIES OF CARBOXYLIC ACIDS

被引：1

作者：

Wada, Koji ^{[1
]}

Goto, Mizuko ^{[1
]}

Yamashita, Hiroshi ^{[1
]}

Nagasawa, Kazuo ^{[1
]}

机构：

[1] Hokkaido Pharmaceut Univ, Sch Pharm, Teine Ku, 7-15-4-1 Maeda, Sapporo, Hokkaido 0068590, Japan

来源：

HETEROCYCLES | 2017年 / 94卷 / 05期

关键词：

Chiral Derivatizing Agent; (S)-4-(3-Aminopyrrolidin-1-yl)coumarin; (S)-4-(3-Aminopiperidin-1-yl)coumarin; (S)-4-(3-Aminoazepan-1-yl)coumarin; ALCOHOLS; AMINES; NMR; DISCRIMINATION; REAGENT;

D O I：

10.3987/COM-17-13683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-4-(3-Aminopyrrolidin-l-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-l-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable H-1 NMR optical purity determination agents for chiral carboxylic acids.

引用

页码：964 / 978

页数：15

共 12 条

[1] CHIRAL DISCRIMINATION BY NMR-SPECTROSCOPY [J].

CASY, AF .

TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1993, 12 (04) :185-189

[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[3] Application of chiral derivatizing agents in the high-performance liquid chromatographic separation of amino acid enantiomers:: A review [J].

Ilisz, Istvan ;

Berkecz, Robert ;

Peter, Antal .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2008, 47 (01) :1-15

[4]

KNAPP DR, 1979, HDB ANAL DERIVATIZAT, P405

[5]

Morrison J. D., 1983, ASYMMETRIC SYNTHESIS, V1, p[13, 59]

[6] Coumarin-containing chiral discriminating agents .7. New crystalline H-1-NMR enantiomeric excess determination reagent for alcohols and amines, (R)-(-)- and (S)-(+)-O-coumarinylmandelic acids [J].

Nagasawa, K ;

Seto, N ;

Hara, C ;

Ito, K .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1997, 117 (10-11) :786-799

[7] A NOVEL AND EFFICIENT SYNTHESIS OF 5-SUBSTITUTED AND 5,6-DISUBSTITUTED 4-METHYLCOUMARINS USING ORGANOCERIUM(III) REAGENTS [J].

NAGASAWA, K ;

KANBARA, H ;

MATSUSHITA, K ;

ITO, K .

TETRAHEDRON LETTERS, 1985, 26 (52) :6477-6480

[8] New crystalline N-(coumarin-4-yl)-L-pyroglutamic acid. The first synthesis and application to H-1 NMR optical purity determination of alcohols and amines [J].

Nagasawa, K ;

Okazaki, R ;

Yamashita, A ;

Ito, K ;

Wada, K .

HETEROCYCLES, 1997, 45 (06) :1047-1050

[9]

NAGASAWA K, 1993, CHEM PHARM BULL, V41, P211

[10] TERT-BUTYL LITHIOACETATE ON ORTHO-HYDROXYPHENONES PROVIDING 2-METHYLCHROMONES - AN EASY ACCESS TO KHELLIN [J].

NAGASAWA, K ;

KANBARA, H ;

MATSUSHITA, K ;

ITO, K .

HETEROCYCLES, 1988, 27 (05) :1159-1162

← 1 2 →