New enzymatic and chemical approaches to enantiopure etodolac

被引:18
作者
Brenna, E
Fuganti, C
Fuganti, D
Grasselli, P
Malpezzi, L
PedrocchiFantoni, G
机构
[1] Dipto. di Chimica del Politecnico, Ctro. CNR Chim. Sostanze O., I-20131 Milano
关键词
D O I
10.1016/S0040-4020(97)10242-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+)- and (-)-etodolac enantiomers were prepared both by classical resolution via crystallisation of diastereoisomeric salts with (+) and (-)-alpha-methylbenzylamine, and by suitable manipulation of derivatives (-)-3- and (+)-4, obtained by lipase-catalysed kinetic resolution of racemic 3. X-ray diffraction analysis of the 4-bromobenzoate derivative of (+)-3, obtained from enantiopure acetate (+)-4, allowed us to determine the absolute (R) configuration of(-)-etodolac. (C) 1997 Elsevier Science Ltd.
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页码:17769 / 17780
页数:12
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共 12 条
  • [1] DIMETHYL SULFOXIDE-ACID ANHYDRIDE MIXTURES . NEW REAGENTS FOR OXIDATION OF ALCOHOLS
    ALBRIGHT, JD
    GOLDMAN, L
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (18) : 4214 - +
  • [2] SIR92 - a program for automatic solution of crystal structures by direct methods
    ALTOMARE, A
    CASCARANO, G
    GIACOVAZZO, G
    GUAGLIARDI, A
    BURLA, MC
    POLIDORI, G
    CAMALLI, M
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 : 435 - 435
  • [3] Asymmetric Friedel-Crafts reaction: An application to the synthesis of an etodolac analogue.
    Cabral, LM
    Costa, PRR
    Vasconcellos, MLAA
    Barreiro, EJ
    Castro, RN
    [J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (19) : 3671 - 3676
  • [4] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [5] DAMERSON CA, 1983, J MED CHEM, V36, P1778
  • [6] ETODOLIC ACID AND RELATED COMPOUNDS - CHEMISTRY AND ANTIINFLAMMATORY ACTIONS OF SOME POTENT DISUBSTITUTED AND TRISUBSTITUTED 1,3,4,9-TETRAHYDROPYRANO[3,4-B]INDOLE-1-ACETIC ACIDS
    DEMERSON, CA
    HUMBER, LG
    PHILIPP, AH
    MARTEL, RR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (03) : 391 - 395
  • [7] ON ENANTIOMORPH-POLARITY ESTIMATION
    FLACK, HD
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV): : 876 - 881
  • [8] ETODOLAC (1,8-DIETHYL-1,3,4,9-TETRAHYDROPYRANO[3,4-B]INDOLE-1-ACETIC ACID) - A POTENT ANTIINFLAMMATORY DRUG - CONFORMATION AND ABSOLUTE-CONFIGURATION OF ITS ACTIVE ENANTIOMER
    HUMBER, LG
    DEMERSON, CA
    SWAMINATHAN, P
    BIRD, PH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (05) : 871 - 874
  • [9] OXIDATION WITH NICKEL PEROXIDE .1. OXIDATION OF ALCOHOLS
    NAKAGAWA, K
    NAKATA, T
    KONAKA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) : 1597 - &
  • [10] POPPE L, 1992, SELECTIVE BIOCATALYS, P141