A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium.

被引:11
作者
Swaminathan, S [1 ]
Singh, AK
Li, WS
Venit, JJ
Natalie, KJ
Simpson, JH
Weaver, RE
Silverberg, LJ
机构
[1] Bristol Myers Squibb, Chem Proc Technol, New Brunswick, NJ 08903 USA
[2] Bristol Myers Squibb, Tech Operat, Syracuse, NY 13221 USA
关键词
D O I
10.1016/S0040-4039(98)00904-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclization of acetal amide was carried out with trimethylsilyl trifluoromethanesulfonate, followed by elimination using sodium methoxide to give 2,5-disubstituted oxazole, thus completing a new route to the cardivascular drug ifetroban sodium. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4769 / 4772
页数:4
相关论文
共 14 条
  • [1] CUPRIC BROMIDE MEDIATED OXIDATION OF 4-CARBOXYOXAZOLINES TO THE CORRESPONDING OXAZOLES
    BARRISH, JC
    SINGH, J
    SPERGEL, SH
    HAN, WC
    KISSICK, TP
    KRONENTHAL, DR
    MUELLER, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) : 4494 - 4496
  • [2] TANTAZOLES - UNUSUAL CYTOTOXIC ALKALOIDS FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE
    CARMELI, S
    MOORE, RE
    PATTERSON, GML
    CORBETT, TH
    VALERIOTE, FA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8195 - 8197
  • [3] TOTAL SYNTHESIS OF (+)-CALYCULIN-A
    EVANS, DA
    GAGE, JR
    LEIGHTON, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) : 9434 - 9453
  • [4] ALLYL ETHER AS A PROTECTING GROUP IN CARBONHYDRATE CHEMISTRY .2.
    GIGG, R
    WARREN, CD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (15): : 1903 - &
  • [5] NEW CHEMISTRY OF OXAZOLES
    HASSNER, A
    FISCHER, B
    [J]. HETEROCYCLES, 1993, 35 (02) : 1441 - 1465
  • [6] JANSEN R, 1992, LIEBIGS ANN CHEM, P357
  • [7] SYNTHESIS AND ANTITUMOR-ACTIVITY OF LIPID-A ANALOGS HAVING A PHOSPHONOOXYETHYL GROUP WITH ALPHA-CONFIGURATION OR BETA-CONFIGURATION AT POSITION-1
    KUSAMA, T
    SOGA, T
    SHIOYA, E
    NAKAYAMA, K
    NAKAJIMA, H
    OSADA, Y
    ONO, Y
    KUSUMOTO, S
    SHIBA, T
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) : 3366 - 3372
  • [8] THE OXIDATION OF 2-OXAZOLINES TO 1,3-OXAZOLES
    MEYERS, AI
    TAVARES, F
    [J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2481 - 2484
  • [9] INTERPHENYLENE 7-OXABICYCLO[2.2.1]HEPTANE OXAZOLES - HIGHLY POTENT, SELECTIVE, AND LONG-ACTING THROMBOXANE A(2)-RECEPTOR ANTAGONISTS
    MISRA, RN
    BROWN, BR
    SHER, PM
    PATEL, MM
    HALL, SE
    HAN, WC
    BARRISH, JC
    KOCY, O
    HARRIS, DN
    GOLDENBERG, HJ
    MICHEL, IM
    SCHUMACHER, WA
    WEBB, ML
    MONSHIZADEGAN, H
    OGLETREE, ML
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) : 1401 - 1417
  • [10] A new synthesis of oxazole derivatives.
    Robinson, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1909, 95 : 2167 - 2174