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
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
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页码:2051 / 2057
页数:7
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