A simple and efficient new approach to the total synthesis of (+/-)-4-amino-3-(4-chlorophenyl)-butyric acid (BACLOFEN)

被引:14
|
作者
Coelho, F
deAzevedo, MBM
Boschiero, R
Resende, P
机构
[1] UNICAMP, Instituto de Química, Depto. de Quim. Orgânica, 13083-970 - Campinas, SP
基金
巴西圣保罗研究基金会;
关键词
D O I
10.1080/00397919708004109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Based on the utilization of a [2+2] cycloaddition reaction between dichloroketene and an appropriated olefin as a key step, we describe a new and simple four step approach to the total synthesis of (+/-)-4-amino-3-(4-chlorophenyl)-butyric acid (BACLOFEN), a selective GABA(B) agonist used as antispastic agent.
引用
收藏
页码:2455 / 2465
页数:11
相关论文
共 50 条
  • [1] AN EFFICIENT SYNTHESIS OF (+/-)-4-AMINO-3-(4-CHLOROPHENYL)-BUTYRIC ACID - (BACLOFEN)
    IBUKA, T
    SCHOENFELDER, A
    BILDSTEIN, P
    MANN, A
    SYNTHETIC COMMUNICATIONS, 1995, 25 (12) : 1777 - 1782
  • [2] (R)-Baclofen [(R)-4-amino-3-(4-chlorophenyl)-butanoic acid]
    Belov, Feodor
    Villinger, Alexander
    von Langermann, Jan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2022, 78 : 33 - +
  • [3] SYNTHESIS OF C-14-LABELED AND TRITIUM-LABELED 4-AMINO-3-(4-CHLOROPHENYL)-BUTYRIC ACID (BACLOFEN)
    KUNG, W
    FAIGLE, JW
    KOCHER, E
    WIRZ, B
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1983, 20 (02): : 213 - 231
  • [4] PREPARATIVE LIQUID-CHROMATOGRAPHIC SEPARATION OF ISOMERS OF 4-AMINO-3-(4-CHLOROPHENYL)BUTYRIC ACID
    VACCHER, C
    BERTHELOT, P
    FLOUQUET, N
    DEBAERT, M
    JOURNAL OF CHROMATOGRAPHY, 1991, 542 (02): : 502 - 507
  • [6] H-1 AND C-13 NMR DETERMINATION OF THE ENANTIOMERIC PURITY OF 4-AMINO-3-(4-CHLOROPHENYL)-BUTYRIC ACID
    VACCHER, C
    BERTHELOT, P
    FLOUQUET, N
    DEBAERT, M
    GUYON, R
    VERMEERSCH, G
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1991, 47 (11): : 1631 - 1632
  • [7] DETERMINATION OF 4-AMINO-3-(PARA-CHLOROPHENYL)BUTYRIC ACID (BACLOFEN) IN PLASMA BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY
    HARRISON, PM
    TONKIN, AM
    MCLEAN, AJ
    JOURNAL OF CHROMATOGRAPHY, 1985, 339 (02): : 424 - 428
  • [8] Synthesis and pharmacology of the baclofen homologues 5-amino-4-(4-chlorophenyl)pentanoic acid and the R- and S-enantiomers of 5-amino-3-(4-chlorophenyl)pentanoic acid
    Karla, R
    Ebert, B
    Thorkildsen, C
    Herdeis, C
    Johansen, TN
    Nielsen, B
    Krogsgaard-Larsen, P
    JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (11) : 2053 - 2059
  • [9] SYNTHESIS OF ANALOGS OF GABA .7. (Z) AND (E)-4-AMINO-3-(4-CHLOROPHENYL)BUT-2-ENOIC ACIDS AS UNSATURATED BACLOFEN DERIVATIVES
    ALLAN, RD
    TRAN, H
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (12) : 2641 - 2645
  • [10] AN EFFICIENT SYNTHESIS OF (+/-)-3-AMINO-2-(4-CHLOROPHENYL)-PROPYLPHOSPHONIC ACID (PHACLOFEN)
    HALL, RG
    SYNTHESIS-STUTTGART, 1989, (06): : 442 - 443