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
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