Optical resolution of baclofen via diastereomeric salt pair formation between 3-(p-chlorophenyl)glutaramic acid and (S)-(-)-alpha-phenylethylamine

被引：26

作者：

Caira, MR ^{[1
]}

Clauss, R ^{[1
]}

Nassimbeni, LR ^{[1
]}

Scott, JL ^{[1
]}

Wildervanck, AF ^{[1
]}

机构：

[1] FINE CHEM CORP, EPPINDUST, SOUTH AFRICA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1997年 / 04期

关键词：

D O I：

10.1039/a606037d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structures of the diastereomeric salts of (R)-(+)- and (S)-(-)-3-(p-chlorophenyl)glutaramic acid with (S)-(-)-phenylethylamine have been determined by X-ray crystallography. Solubility and melting behaviours of the salts were analysed and correlated with their structural properties in the solid state, The (R)-(+)-3-(p-chlorophenyl)glutaramic acid was converted to (R)-(-)-baclofen via a Hofmann degradation (57% yield, 99.8% ee, enantiomeric excess).

引用

收藏

页码：763 / 768

页数：6

相关论文

共 30 条

[21]

SIVOV NA, 1981, OTKRYTIYA IZOBRET PR, V17, P88

[22]

SOBOCINSKA M, 1974, ROCZ CHEM, V48, P461

[23] THE GEOMETRY OF THE N-H ... O=C HYDROGEN-BOND .3. HYDROGEN-BOND DISTANCES AND ANGLES [J].

TAYLOR, R ;

KENNARD, O ;

VERSICHEL, W .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1984, 40 (JUN) :280-288

[24] Chiral lock and chiral key in inclusion crystals [J].

Toda, F .

SUPRAMOLECULAR CHEMISTRY, 1995, 6 (1-2) :159-163

[25] DIRECT SEPARATION OF 4-AMINO-3-(4-CHLOROPHENYL)BUTYRIC ACID AND ANALOGS, GABA(B) LIGANDS, USING A CHIRAL CROWN-ETHER STATIONARY-PHASE [J].

VACCHER, C ;

BERTHELOT, P ;

DEBAERT, M .

JOURNAL OF CHROMATOGRAPHY, 1993, 645 (01) :95-99

[26] LONE-PAIR DIRECTIONALITY IN HYDROGEN-BOND POTENTIAL FUNCTIONS FOR MOLECULAR MECHANICS CALCULATIONS - THE INHIBITION OF HUMAN CARBONIC ANHYDRASE-II BY SULFONAMIDES [J].

VEDANI, A ;

DUNITZ, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7653-7658

[27] ENANTIOSELECTIVE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC DETERMINATION OF BACLOFEN AFTER DERIVATIZATION WITH A CHIRAL ADDUCT OF ORTHO-PHTHALDIALDEHYDE [J].

WUIS, EW ;

KOLMER, EWJB ;

VANBEIJSTERVELDT, LEC ;

BURGERS, RCM ;

VREE, TB ;

VANDERKLEYN, E .

JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1987, 415 (02) :419-422

[28]

YOSHIFUJI S, 1995, CHEM PHARM BULL, V43, P1302

[29] OPTICAL RESOLUTION, CHARACTERIZATION, AND X-RAY CRYSTAL-STRUCTURES OF DIASTEREOMERIC SALTS OF CHIRAL AMINO-ACIDS WITH (S)-(-)-1-PHENYLETHANESULFONIC ACID [J].

YOSHIOKA, R ;

OHTSUKI, O ;

DATE, T ;

OKAMURA, K ;

SENUMA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (11) :3012-3020

[30] LAZY PULVERIX, A COMPUTER-PROGRAM, FOR CALCULATING X-RAY AND NEUTRON-DIFFRACTION POWDER PATTERNS [J].

YVON, K ;

JEITSCHKO, W ;

PARTHE, E .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1977, 10 (FEB1) :73-74