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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).
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页码:2051 / 2057
页数:7
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