A CONVENIENT SYNTHESIS OF CHIRAL OXAZOLIDIN-2-ONES AND THIAZOLIDIN-2-ONES AND AN IMPROVED PREPARATION OF TRIPHOSGENE

被引:30
作者
FALB, E [1 ]
NUDELMAN, A [1 ]
HASSNER, A [1 ]
机构
[1] BAR ILAN UNIV,DEPT CHEM,IL-52900 RAMAT GAN,ISRAEL
关键词
D O I
10.1080/00397919308012605
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxazolidin-2-ones and thiazolidin-2-one are conveniently prepared by condensation of L-serine, L-threonine and L-cysteine, respectively with triphosgene. The corresponding methyl esters may be subsequently obtained by quenching the reaction mixture with methanol, without prior need for the isolation of the free acids. An improved procedure for preparation of triphosgene using an internal cooling system is described.
引用
收藏
页码:2839 / 2844
页数:6
相关论文
共 12 条
  • [1] CHEN ST, 1990, INT J PEPT PROT RES, V35, P52
  • [2] TRIPHOSGENE, A CRYSTALLINE PHOSGENE SUBSTITUTE
    ECKERT, H
    FORSTER, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (09): : 894 - 895
  • [3] REACTIONS OF POLYFUNCTIONAL AMINO-ACIDS WITH N,N'-CARBONYLDIIMIDAZOLE IN AQUEOUS-SOLUTION - OLIGOPEPTIDE FORMATION
    EHLER, KW
    GIRARD, E
    ORGEL, LE
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1977, 491 (01) : 253 - 264
  • [4] L-2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID AND GLUTATHIONE IN HUMAN-IMMUNODEFICIENCY-VIRUS
    GIORGI, G
    MICHELI, L
    FIASCHI, AI
    CERRETANI, D
    ROMEO, R
    DALPRA, P
    BOZZO, M
    [J]. CURRENT THERAPEUTIC RESEARCH-CLINICAL AND EXPERIMENTAL, 1992, 52 (03): : 461 - 467
  • [5] KANEKO T, 1962, B CHEM SOC JPN, V37, P242
  • [6] KOMIVES T, 1989, ORG PREP PROCED INT, V21, P251
  • [7] 2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID AND RELATED SUBSTANCES
    MACLAREN, JA
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (07) : 1891 - &
  • [8] SHAH H, 1979, CANCER RES, V39, P3942
  • [9] A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE
    SIBI, MP
    RENHOWE, PA
    [J]. TETRAHEDRON LETTERS, 1990, 31 (51) : 7407 - 7410
  • [10] TOTAL SYNTHESIS OF (+)-LATRUNCULIN-A
    WHITE, JD
    KAWASAKI, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4991 - 4993