메뉴 건너뛰기




Volumn 50, Issue 10, 2011, Pages 5982-5991

Combined in situ monitoring method for analysis and optimization of the lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide

Author keywords

[No Author keywords available]

Indexed keywords

ATR FTIR; DYNAMIC BEHAVIORS; END POINTS; IN-SITU MONITORING; IN-SITU SPECTROSCOPY; LITHIATION; LOW TEMPERATURE REACTIONS; OPTIMIZED REACTION CONDITIONS; POTENT INHIBITOR; REACTION CALORIMETRY; REACTION MECHANISM; REACTION STEPS; REVERSE TRANSCRIPTASES;

EID: 79955926668     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie102407h     Document Type: Article
Times cited : (4)

References (43)
  • 1
    • 33746914340 scopus 로고    scopus 로고
    • Emerging technologies supporting chemical process R and D and their increasing impact on productivity in the pharmaceutical industry
    • DOI 10.1021/cr040674i
    • Rubin, A. E.; Tummala, S.; Both, D. A.; Wang, C.; Delaney, E. J. Emerging Technologies Supporting Chemical Process R&D and Their Increasing Impact on Productivity in the Pharmaceutical Industry Chem. Rev. 2006, 106 (7) 2794-2810 (Pubitemid 44193046)
    • (2006) Chemical Reviews , vol.106 , Issue.7 , pp. 2794-2810
    • Rubin, A.E.1    Tummala, S.2    Both, D.A.3    Wang, C.4    Delaney, E.J.5
  • 2
    • 79955902782 scopus 로고    scopus 로고
    • Future Trends for PAT for Increased Process Understanding and Growing Applications in Biomanufacturing
    • John Wiley & Sons, Ltd: New York
    • Bakeev, K. A.; Menezes, J. C., Future Trends for PAT for Increased Process Understanding and Growing Applications in Biomanufacturing. In Process Analytical Technology; Bakeev, K. A., Ed.; John Wiley & Sons, Ltd: New York, 2010; pp 521 - 543.
    • (2010) Process Analytical Technology , pp. 521-543
    • Bakeev, K.A.1    Menezes, J.C.2    Bakeev, K.A.3
  • 3
    • 79955917592 scopus 로고    scopus 로고
    • Experimental Techniques
    • Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany
    • Stoessel, F. Experimental Techniques. In Thermal Safety of Chemical Processes; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; pp 81 - 100.
    • (2008) Thermal Safety of Chemical Processes , pp. 81-100
    • Stoessel, F.1
  • 5
    • 72449152645 scopus 로고    scopus 로고
    • A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction
    • Girgis, M. J.; Liang, J. K.; Du, Z.; Slade, J.; Prasad, K. A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction Org. Process Res. Dev. 2009, 13 (6) 1094-1099
    • (2009) Org. Process Res. Dev. , vol.13 , Issue.6 , pp. 1094-1099
    • Girgis, M.J.1    Liang, J.K.2    Du, Z.3    Slade, J.4    Prasad, K.5
  • 6
    • 0031557565 scopus 로고    scopus 로고
    • FTIR and calorimetric analyses of the specific interactions in poly(ε-caprolactone)/poly(styrene-co-acrylonitrile) blends using low molecular weight analogues
    • Svoboda, P.; Kressler, J.; Ougizawa, T.; Inoue, T. FTIR and Calorimetric Analyses of the Specific Interactions in Poly(-caprolactone)/Poly(styrene-co- acrylonitrile) Blends Using Low Molecular Weight Analogues Macromolecules 1997, 30 (7) 1973-1979 (Pubitemid 127564887)
    • (1997) Macromolecules , vol.30 , Issue.7 , pp. 1973-1979
    • Svoboda, P.1    Kreesler, J.2    Ougizawa, T.3    Inoue, T.4    Ozutsumi, K.5
  • 7
    • 0035532811 scopus 로고    scopus 로고
    • Determination of Reaction Parameters Using a Small Calorimeter with an Integrated FT-IR Probe and Parameter Fitting
    • Pastré, J.; Zogg, A.; Fischer, U.; Hungerbühler, K. Determination of Reaction Parameters Using a Small Calorimeter with an Integrated FT-IR Probe and Parameter Fitting Org. Process Res. Dev. 2001, 5 (2) 158-166
    • (2001) Org. Process Res. Dev. , vol.5 , Issue.2 , pp. 158-166
    • Pastré, J.1    Zogg, A.2    Fischer, U.3    Hungerbühler, K.4
  • 8
    • 2342607144 scopus 로고    scopus 로고
    • A Combined Approach using Calorimetry and IR-ATR Spectroscopy for the Determination of Kinetic and Thermodynamic Reaction Parameters
    • ETH Zürich: Zürich
    • Zogg, A. A Combined Approach using Calorimetry and IR-ATR Spectroscopy for the Determination of Kinetic and Thermodynamic Reaction Parameters. Diss ETH Zurich No 15086; ETH Zürich: Zürich, 2003.
    • (2003) Diss ETH Zurich No 15086
    • Zogg, A.1
  • 9
    • 79955916814 scopus 로고    scopus 로고
    • UV-Visible Spectroscopy for On-Line Analysis
    • John Wiley & Sons, Ltd: New York
    • Liauw, M. A.; Baylor, L. C.; ORourke, P. E., UV-Visible Spectroscopy for On-Line Analysis. In Process Analytical Technology, Bakeev, K. A., Ed.; John Wiley & Sons, Ltd: New York, 2010; pp 81 - 106.
    • (2010) Process Analytical Technology , pp. 81-106
    • Liauw, M.A.1    Baylor, L.C.2    Orourke, P.E.3    Bakeev, K.A.4
  • 10
    • 69349087889 scopus 로고    scopus 로고
    • Kinetic hard-modelling and spectral validation of rank-deficient spectroscopic data: A case study
    • Billeter, J.; Neuhold, Y.-M.; Hungerbühler, K. Kinetic hard-modelling and spectral validation of rank-deficient spectroscopic data: A case study Chemom. Intell. Lab. Syst. 2009, 98 (2) 213-226
    • (2009) Chemom. Intell. Lab. Syst. , vol.98 , Issue.2 , pp. 213-226
    • Billeter, J.1    Neuhold, Y.-M.2    Hungerbühler, K.3
  • 11
    • 67349131140 scopus 로고    scopus 로고
    • Comparison of external bulk video imaging with focused beam reflectance measurement and ultra-violet visible spectroscopy for metastable zone identification in food and pharmaceutical crystallization processes
    • Simon, L. L.; Nagy, Z. K.; Hungerbühler, K. Comparison of external bulk video imaging with focused beam reflectance measurement and ultra-violet visible spectroscopy for metastable zone identification in food and pharmaceutical crystallization processes Chem. Eng. Sci. 2009, 64 (14) 3344-3351
    • (2009) Chem. Eng. Sci. , vol.64 , Issue.14 , pp. 3344-3351
    • Simon, L.L.1    Nagy, Z.K.2    Hungerbühler, K.3
  • 12
    • 72449178344 scopus 로고    scopus 로고
    • Endoscopy-Based in Situ Bulk Video Imaging of Batch Crystallization Processes
    • Simon, L. L.; Nagy, Z. K.; Hungerbühler, K. Endoscopy-Based in Situ Bulk Video Imaging of Batch Crystallization Processes Org. Process Res. Dev. 2009, 13 (6) 1254-1261
    • (2009) Org. Process Res. Dev. , vol.13 , Issue.6 , pp. 1254-1261
    • Simon, L.L.1    Nagy, Z.K.2    Hungerbühler, K.3
  • 13
    • 77949284961 scopus 로고    scopus 로고
    • Organolithium in Asymmetric Processes
    • Wu, G.; Huang, M. Organolithium in Asymmetric Processes Top. Organomet. Chem. 2004, 6, 1-35
    • (2004) Top. Organomet. Chem. , vol.6 , pp. 1-35
    • Wu, G.1    Huang, M.2
  • 14
    • 33746907049 scopus 로고    scopus 로고
    • Organolithium reagents in pharmaceutical asymmetric processes
    • DOI 10.1021/cr040694k
    • Wu, G.; Huang, M. Organolithium reagents in pharmaceutical asymmetric processes Chem. Rev. 2006, 106, 2596-2616 (Pubitemid 44193043)
    • (2006) Chemical Reviews , vol.106 , Issue.7 , pp. 2596-2616
    • Wu, G.1    Huang, M.2
  • 15
    • 0000679903 scopus 로고    scopus 로고
    • Regioselective, Diastereoselective, and Enantioselective Lithiation-Substitution Sequences: Reaction Pathways and Synthetic Applications
    • Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Regioselective, Diastereoselective, and Enantioselective Lithiation-Substitution Sequences: Reaction Pathways and Synthetic Applications Acc. Chem. Res. 1996, 29 (11) 552-560 (Pubitemid 126453246)
    • (1996) Accounts of Chemical Research , vol.29 , Issue.11 , pp. 552-560
    • Beak, P.1    Basu, A.2    Gallagher, D.J.3    Park, Y.S.4    Thayumanavan, S.5
  • 17
    • 0028788312 scopus 로고
    • Use of an Ephedrine Alkoxide to Mediate Enantioselective Addition of an Acetylide to a Prochiral Ketone: Asymmetric Synthesis of the Reverse Transcriptase Inhibitor L-743,726
    • Thompson, A. S.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J. Use of an Ephedrine Alkoxide to Mediate Enantioselective Addition of an Acetylide to a Prochiral Ketone: Asymmetric Synthesis of the Reverse Transcriptase Inhibitor L-743,726 Tetrahedron Lett. 1995, 36 (49) 8937-8940
    • (1995) Tetrahedron Lett. , vol.36 , Issue.49 , pp. 8937-8940
    • Thompson, A.S.1    Corley, E.G.2    Huntington, M.F.3    Grabowski, E.J.J.4
  • 19
    • 33845560452 scopus 로고
    • Ortho Functionalization of Aromatic Amines: Ortho Lithiation of N-Pivaloylanilines
    • Fuhrer, W.; Gschwend, H. W. Ortho Functionalization of Aromatic Amines: Ortho Lithiation of N-Pivaloylanilines J. Org. Chem. 1979, 44 (7) 1133-1136
    • (1979) J. Org. Chem. , vol.44 , Issue.7 , pp. 1133-1136
    • Fuhrer, W.1    Gschwend, H.W.2
  • 21
    • 0012397313 scopus 로고
    • Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics
    • Snieckus, V. Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics Chem. Rev. 1990, 90 (6) 879-933
    • (1990) Chem. Rev. , vol.90 , Issue.6 , pp. 879-933
    • Snieckus, V.1
  • 22
    • 0000371989 scopus 로고
    • Stabilities of some n-alkyllithium compounds in mixed solvent systems
    • Gilman, H.; Schwebke, G. L. Stabilities of some n-alkyllithium compounds in mixed solvent systems J. Organomet. Chem. 1965, 4 (6) 483-487
    • (1965) J. Organomet. Chem. , vol.4 , Issue.6 , pp. 483-487
    • Gilman, H.1    Schwebke, G.L.2
  • 23
    • 0001630249 scopus 로고    scopus 로고
    • Half-Lives of Organolithium Reagents in Common Ethereal Solvents
    • Stanetty, P.; Mihovilovic, M. D. Half-Lives of Organolithium Reagents in Common Ethereal Solvents J. Org. Chem. 1997, 62 (5) 1514-1515
    • (1997) J. Org. Chem. , vol.62 , Issue.5 , pp. 1514-1515
    • Stanetty, P.1    Mihovilovic, M.D.2
  • 25
    • 77952893922 scopus 로고    scopus 로고
    • Nonisothermal Calorimetry for Fast Thermokinetic Reaction Analysis: Solvent-Free Esterification of n-Butanol by Acetic Anhydride
    • Richner, G.; Neuhold, Y.-M.; Hungerbühler, K. Nonisothermal Calorimetry for Fast Thermokinetic Reaction Analysis: Solvent-Free Esterification of n-Butanol by Acetic Anhydride Org. Process Res. Dev. 2010, 14 (3) 524-536
    • (2010) Org. Process Res. Dev. , vol.14 , Issue.3 , pp. 524-536
    • Richner, G.1    Neuhold, Y.-M.2    Hungerbühler, K.3
  • 26
    • 5144220601 scopus 로고    scopus 로고
    • A pressure-resistant small-scale reaction calorimeter that combines the principles of power compensation and heat balance (CRC.v4)
    • DOI 10.1021/op049900g
    • Visentin, F.; Gianoli, S. I.; Zogg, A.; Kut, O. M.; Hungerbühler, K. A Pressure-Resistant Small-Scale Reaction Calorimeter That Combines the Principles of Power Compensation and Heat Balance (CRC.v4) Org. Process Res. Dev. 2004, 8 (5) 725-737 (Pubitemid 39345686)
    • (2004) Organic Process Research and Development , vol.8 , Issue.5 , pp. 725-737
    • Visentin, F.1    Gianoli, S.I.2    Zogg, A.3    Kut, O.M.4    Hungerbuhler, K.5
  • 30
    • 79955889758 scopus 로고    scopus 로고
    • NIST Standard Reference Database 69: NIST Chemistry WebBook. (accessed March 2011)
    • NIST Standard Reference Database 69: NIST Chemistry WebBook. http://webbook.nist.gov/chemistry/ (accessed March 2011).
  • 31
    • 77954620097 scopus 로고    scopus 로고
    • Bulk video imaging based multivariate image analysis, process control chart and acoustic signal assisted nucleation detection
    • Simon, L. L.; Abbou Oucherif, K.; Nagy, Z. K.; Hungerbühler, K. Bulk video imaging based multivariate image analysis, process control chart and acoustic signal assisted nucleation detection Chem. Eng. Sci. 2010, 65 (17) 4983-4995
    • (2010) Chem. Eng. Sci. , vol.65 , Issue.17 , pp. 4983-4995
    • Simon, L.L.1    Abbou Oucherif, K.2    Nagy, Z.K.3    Hungerbühler, K.4
  • 32
    • 0000759094 scopus 로고
    • The analysis of organolithium compounds
    • Gilman, H.; Cartledge, F. K. The analysis of organolithium compounds J. Organomet. Chem. 1964, 2 (6) 447-454
    • (1964) J. Organomet. Chem. , vol.2 , Issue.6 , pp. 447-454
    • Gilman, H.1    Cartledge, F.K.2
  • 33
    • 5144228830 scopus 로고    scopus 로고
    • Isothermal reaction calorimetry as a tool for kinetic analysis
    • Zogg, A.; Stoessel, F.; Fischer, U.; Hungerbühler, K. Isothermal reaction calorimetry as a tool for kinetic analysis Thermochim. Acta 2004, 419 (1-2) 1-17
    • (2004) Thermochim. Acta , vol.419 , Issue.1-2 , pp. 1-17
    • Zogg, A.1    Stoessel, F.2    Fischer, U.3    Hungerbühler, K.4
  • 36
    • 0001185584 scopus 로고
    • Electrochemical Determination of the pKa of Weak Acids in N,N-Dimethylformamide
    • Maran, F.; Celadon, D.; Severin, M. G.; Vianello, E. Electrochemical Determination of the pKa of Weak Acids in N,N-Dimethylformamide J. Am. Chem. Soc. 1991, 113 (24) 9320-9329
    • (1991) J. Am. Chem. Soc. , vol.113 , Issue.24 , pp. 9320-9329
    • Maran, F.1    Celadon, D.2    Severin, M.G.3    Vianello, E.4
  • 37
    • 33846064670 scopus 로고    scopus 로고
    • a values of C-H bonds in aromatic heterocyclic compounds in DMSO?
    • DOI 10.1016/j.tet.2006.12.032, PII S0040402006019429
    • Shen, K.; Fu, Y.; Li, J. N.; Liu, L.; Guo, Q. X. What are the pKa values of C-H bonds in aromatic heterocyclic compounds in DMSO? Tetrahedron 2007, 63 (7) 1568-1576 (Pubitemid 46074114)
    • (2007) Tetrahedron , vol.63 , Issue.7 , pp. 1568-1576
    • Shen, K.1    Fu, Y.2    Li, J.-N.3    Liu, L.4    Guo, Q.-X.5
  • 38
    • 0345908766 scopus 로고
    • Standard molar enthalpies of formation of lithium alkoxides
    • Leal, J. P.; Simões, J. A. M. Standard molar enthalpies of formation of lithium alkoxides J. Organomet. Chem. 1993, 460 (2) 131-138
    • (1993) J. Organomet. Chem. , vol.460 , Issue.2 , pp. 131-138
    • Leal, J.P.1    Simões, J.A.M.2
  • 39
    • 59349099034 scopus 로고    scopus 로고
    • Rayleigh, Mie, and Tyndall scatterings of polystyrene microspheres in water: Wavelength, size, and angle dependences
    • He, G. S.; Qin, H.-Y.; Zheng, Q. Rayleigh, Mie, and Tyndall scatterings of polystyrene microspheres in water: Wavelength, size, and angle dependences J. Appl. Phys. 2009, 105 (2) 023110-10
    • (2009) J. Appl. Phys. , vol.105 , Issue.2 , pp. 023110-10
    • He, G.S.1    Qin, H.-Y.2    Zheng, Q.3
  • 40
    • 20344378977 scopus 로고    scopus 로고
    • Experimental and theoretical analysis of Friedel-Crafts acylation of thioanisole to 4-(methylthio)acetophenone using solid acids
    • DOI 10.1016/j.molcata.2005.04.001, PII S1381116905002177
    • Yadav, G. D.; Bhagat, R. D. Experimental and theoretical analysis of Friedel-Crafts acylation of thioanisole to 4-(methylthio)acetophenone using solid acids J. Mol. Catal A: Chem. 2005, 235 (1-2) 98-107 (Pubitemid 40785902)
    • (2005) Journal of Molecular Catalysis A: Chemical , vol.235 , Issue.1-2 , pp. 98-107
    • Yadav, G.D.1    Bhagat, R.D.2
  • 41
    • 0037763698 scopus 로고    scopus 로고
    • Kinetic studies on Friedel-Crafts acylation of anisole by clayzic
    • Selvin, R.; Sivasankar, B.; Rengaraj, K. Kinetic studies on Friedel-Crafts acylation of anisole by clayzic React. Kinet. Catal. Lett. 1999, 67 (2) 319-324
    • (1999) React. Kinet. Catal. Lett. , vol.67 , Issue.2 , pp. 319-324
    • Selvin, R.1    Sivasankar, B.2    Rengaraj, K.3
  • 42
    • 0038238229 scopus 로고    scopus 로고
    • Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway
    • Allegretti, P. E.; Bravo, R. D.; Furlong, J. J. P. Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway Kinet. Catal. 2002, 43 (6) 764-773
    • (2002) Kinet. Catal. , vol.43 , Issue.6 , pp. 764-773
    • Allegretti, P.E.1    Bravo, R.D.2    Furlong, J.J.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.