Scale-up of Azide Chemistry: A Case Study

被引：32

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

共 50 条

[1] Continuous flow azide formation: Optimization and scale-up
Delville, Marielle M. E.
Nieuwland, Pieter J.
Janssen, Paul
Koch, Kaspar
van Hest, Jan C. M.
Rutjes, Floris P. J. T.
CHEMICAL ENGINEERING JOURNAL, 2011, 167 (2-3) : 556 - 559
[2] Personal chemistry adds scale-up
不详
CHEMICAL & ENGINEERING NEWS, 2002, 80 (38) : 21 - 21
[3] Tackling flow chemistry scale-up
Drahl, Carmen
CHEMICAL & ENGINEERING NEWS, 2018, 96 (11) : 10 - 10
[4] A calorimetric investigation to safely scale-up a Curtius rearrangement of acryloyl azide
Ende, DJA
DeVries, KM
Clifford, PJ
Brenek, SJ
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1998, 2 (06) : 382 - 392
[5] A study on the scale-up of acyl azide synthesis in various continuous flow reactors in homogeneous and biphasic systems
Cloudius R. Sagandira
Paul Watts
Journal of Flow Chemistry, 2018, 8 : 69 - 79
[6] A study on the scale-up of acyl azide synthesis in various continuous flow reactors in homogeneous and biphasic systems
Sagandira, Cloudius R.
Watts, Paul
JOURNAL OF FLOW CHEMISTRY, 2018, 8 (02) : 69 - 79
[7] STUDY ON THE SCALE-UP EFFECT OF CYCLONES
周理
刘广春
徐越平
Chinese Journal of Chemical Engineering, 1992, (01) : 67 - 74
[8] The Sequential Scale-Up of an Evidence-Based Intervention: A Case Study
Thomas, Jaime
Cook, Thomas D.
Klein, Alice
Starkey, Prentice
DeFlorio, Lydia
EVALUATION REVIEW, 2018, 42 (03) : 318 - 357
[9] Binol scale-up and repeatability study
Lefler, JL
Cole, J
LC GC NORTH AMERICA, 2006, : 56 - 57
[10] SCALE-UP OF AGITATED VESSELS IN THE CASE OF SUSPENSIONS
KNEULE, F
CHEMIE INGENIEUR TECHNIK, 1983, 55 (04) : 275 - 281

← 1 2 3 4 5 →