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

页码：2051 / 2057

页数：7

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