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Volumn 16, Issue 12, 2012, Pages 2051-2057

Scale-up of azide chemistry: A case study

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE CHEMISTRY; DESYM-METRIZATION; ENANTIOSELECTIVE; HYDRAZOIC ACID; PALLADIUM-CATALYZED; RESEARCH AND DEVELOPMENT; SCALE-UP; TRIMETHYLSILYLAZIDE;

EID: 84871569403     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op3002646     Document Type: Article
Times cited : (36)

References (54)
  • 12
    • 0010351234 scopus 로고
    • The heuristic of violent decomposition expected for azido compounds having a (C + O)/N ratio of <3 is typically used as a qualitative measure of risk: Smith, P. A. S. The Chemistry of Open-Chain Organic Nitrogen Compounds; W. A. Benjamin Inc.: New York, USA, 1966; Vol. II, pp 211-256.
    • (1966) The Chemistry of Open-Chain Organic Nitrogen Compounds , vol.2 , pp. 211-256
    • Smith, P.A.S.1
  • 13
    • 84891572017 scopus 로고    scopus 로고
    • Nonetheless, reactions involving azide intermediates must be first conducted in small laboratory scale and evaluated with specialized equipment before considering additional development. For a discussion: Keicher, T.; Löbbecke, S. Organic Azides: Synthesis and Applications; Bräse, S.; Banert, K., Eds.; Wiley-VCH: Weinheim, 2010; pp 3-27.
    • (2010) Organic Azides: Synthesis and Applications , pp. 3-27
    • Keicher, T.1    Löbbecke, S.2
  • 18
    • 84871584305 scopus 로고    scopus 로고
    • NIOSH (National Institute for Occupational Safety and Health), International Chemical Safety Cards No. 09050, Recommended Exposure Limits (REL)
    • NIOSH (National Institute for Occupational Safety and Health), International Chemical Safety Cards No. 09050, Recommended Exposure Limits (REL), 1997.
    • (1997)
  • 43
    • 46449138435 scopus 로고    scopus 로고
    • Wiley-VCH: ARC: Accelerating Rate Calorimeter. C80: Setaram C80 Calvet Calorimeter. ADT 24: Temperature at which time to maximum rate at adiabatic conditions is 24 h. AKTS: Advanced Kinetics and Technology Solutions Thermokinetics Software
    • Stoessel, F. Thermal Safety of Chemical Processes: Risk Assessment and Process Design; Wiley-VCH: 2008; pp 66-67. ARC: Accelerating Rate Calorimeter. C80: Setaram C80 Calvet Calorimeter. ADT 24: Temperature at which time to maximum rate at adiabatic conditions is 24 h. AKTS: Advanced Kinetics and Technology Solutions Thermokinetics Software.
    • (2008) Thermal Safety of Chemical Processes: Risk Assessment and Process Design , pp. 66-67
    • Stoessel, F.1
  • 44
    • 84989509374 scopus 로고
    • Low temperatures are also required in order to prevent a [3,3]-sigmatropic rearrangement that results in formation of the 1,2-disubstituted adduct. While this is more pronounced for the five-membered ring series, Trost, B. M.; Stenkamp, D.; Pulley, S. R. Chem.-Eur. J. 1995, 1, 568-562, we also observed it for the six-membered ring upon holding the reaction mixture at room temperature for extended periods of time.
    • (1995) Chem. - Eur. J. , vol.1 , pp. 568-562
    • Trost, B.M.1    Stenkamp, D.2    Pulley, S.R.3
  • 45
    • 0000363937 scopus 로고
    • Alternative conditions for the reduction of the allylic azide were evaluated including hydrogenation and thiol-based methods. Nevertheless, the Staudinger reaction proved superior in terms of rate, overall impurity profile, and process control. Different phosphines can be used in the Staudinger reaction: Gololobov, Y. G.; Zhmurova, I. N.; Kasukn, I. F. Tetrahedron 1980, 37, 437-472
    • (1980) Tetrahedron , vol.37 , pp. 437-472
    • Gololobov, Y.G.1    Zhmurova, I.N.2    Kasukn, I.F.3
  • 46
    • 0035537542 scopus 로고    scopus 로고
    • IPAc was chosen as the solvent for the Boc-protection to facilitate the solvent exchanged to IPA required for the crystallization and to minimize unit operations and cycle time. Chen, C.-K.; Singh, A. K. Org. Process Res. Dev. 2001, 5, 508-513.
    • (2001) Org. Process Res. Dev. , vol.5 , pp. 508-513
    • Chen, C.-K.1    Singh, A.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.