Scale-up of Azide Chemistry: A Case Study

被引：34
作者：
Gonzalez-Bobes, Francisco [1 ]
Kopp, Nathaniel [1 ]
Li, Li [2 ]
Deerberg, Joers [1 ]
Sharma, Praveen [1 ]
Leung, Simon [3 ]
Davies, Merrill [1 ]
Bush, Joseph [3 ]
Hamm, Jason [3 ]
Hrytsak, Michael [3 ]
机构：
[1] Bristol Myers Squibb Co, Chem Dev, New Brunswick, NJ 08903 USA
[2] Bristol Myers Squibb Co, Analyt & Bioanalyt Dev, New Brunswick, NJ 08903 USA
[3] Bristol Myers Squibb Co, Chem Dev Operat, New Brunswick, NJ 08903 USA
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2012年 / 16卷 / 12期
关键词：
HYDRAZOIC ACID; ENANTIOSELECTIVE SYNTHESIS; SAFE; DIAZIDOMETHANE; DECOMPOSITION; EQUILIBRIUM; EXPLOSION;
D O I：
10.1021/op3002646
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
We report research and development conducted to enable the safe implementation of a highly enantioselective palladium-catalyzed desymmetrization of a meso-bis-ester using trimethylsilylazide (TMSN3) as the nucleophile. This work is used as a case example to discuss safe practices when considering the use of azide reagents or intermediates, with a focus on the thermodynamic and quantitative analysis of the hazards associated with hydrazoic acid (HN3).
引用
收藏
页码：2051 / 2057
页数：7
相关论文
共 53 条
  • [1] INFRARED STUDIES OF AZIDE BOUND TO MYOGLOBIN AND HEMOGLOBIN - TEMPERATURE DEPENDENCE OF IONICITY
    ALBEN, JO
    FAGER, LY
    [J]. BIOCHEMISTRY, 1972, 11 (05) : 842 - &
  • [2] Practical Enantioselective Synthesis of a 3-Aryl-3-trifluoromethyl-2-aminopropanol Derivative
    Alimardanov, Asaf
    Nikitenko, Antonia
    Connolly, Terrence J.
    Feigelson, Gregg
    Chan, Anita W.
    Ding, Zhixian
    Ghosh, Mousumi
    Shi, Xinxu
    Ren, Jianxin
    Hansen, Eric
    Farr, Roger
    MacEwan, Michael
    Tadayon, Sam
    Springer, Dane M.
    Kreft, Anthony F.
    Ho, Douglas M.
    Potoski, John R.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (06) : 1161 - 1168
  • [3] [Anonymous], 1989, ULLMANNS ENCYCLOPEDI, VA13, P193
  • [4] Henry's law coefficient of hydrazoic acid
    Betterton, EA
    Robinson, JL
    [J]. JOURNAL OF THE AIR & WASTE MANAGEMENT ASSOCIATION, 1997, 47 (11): : 1216 - 1219
  • [5] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION
    BORDWELL, FG
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) : 456 - 463
  • [6] SELECTIVE EXAMINATION OF HEME PROTEIN AZIDE LIGAND DISTAL GLOBIN INTERACTIONS BY VIBRATIONAL CIRCULAR-DICHROISM
    BORMETT, RW
    ASHER, SA
    LARKIN, PJ
    GUSTAFSON, WG
    RAGUNATHAN, N
    FREEDMAN, TB
    NAFIE, LA
    BALASUBRAMANIAN, S
    BOXER, SG
    YU, NT
    GERSONDE, K
    NOBLE, RW
    SPRINGER, BA
    SLIGAR, SG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) : 6864 - 6867
  • [7] How azide inhibits ATP hydrolysis by the F-ATPases
    Bowler, Matthew W.
    Montgomery, Martin G.
    Leslie, Andrew G. W.
    Walker, John E.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (23) : 8646 - 8649
  • [8] Organic azides:: An exploding diversity of a unique class of compounds
    Bräse, S
    Gil, C
    Knepper, K
    Zimmermann, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
  • [9] Brase S., 2010, Organic Azides, Syntheses and Applications
  • [10] Human health effects of sodium azide exposure: A literature review and analysis
    Chang, SJ
    Lamm, SH
    [J]. INTERNATIONAL JOURNAL OF TOXICOLOGY, 2003, 22 (03) : 175 - 186
123456