Development of a Continuous Flow Process for a Matteson Reaction: From Lab Scale to Full-Scale Production of a Pharmaceutical Intermediate
Within this paper, we present the design, development, and scale-up of a process for a continuous Matteson reaction to produce a key intermediate toward the β-lactamase inhibitor vaborbactam. This includes the successful implementation of the continuous concept at a multiton production scale for the...
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| Published in: | Organic process research & development Vol. 23; no. 5; pp. 1069 - 1077 |
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| Main Authors: | , , , , , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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American Chemical Society
17-05-2019
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| Abstract | Within this paper, we present the design, development, and scale-up of a process for a continuous Matteson reaction to produce a key intermediate toward the β-lactamase inhibitor vaborbactam. This includes the successful implementation of the continuous concept at a multiton production scale for the API at Patheon, part of Thermo Fisher Scientific. The first-generation continuous flow production with its discontinuous downstream processing was further developed to a fully continuous production through installation of a continuous loop reactor. This enabled increased productivity and energy efficiency, eliminated volume and time bottlenecks, and reduced waste. |
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| AbstractList | Within this paper, we present the design, development, and scale-up of a process for a continuous Matteson reaction to produce a key intermediate toward the β-lactamase inhibitor vaborbactam. This includes the successful implementation of the continuous concept at a multiton production scale for the API at Patheon, part of Thermo Fisher Scientific. The first-generation continuous flow production with its discontinuous downstream processing was further developed to a fully continuous production through installation of a continuous loop reactor. This enabled increased productivity and energy efficiency, eliminated volume and time bottlenecks, and reduced waste. |
| Author | Ritzen, Bas Stueckler, Clemens Pabst, Thomas Hermsen, Peter Winkler, Georg Pelz, Andreas Zinganell, Christopher Goldbach, Michel Schuster, Christian de Vries, André Vasiloiu, Maria Poechlauer, Peter Boyer, Serge Steinhofer, Stefan LaVopa, Vito Felfer, Ulfried Hecker, Scott |
| AuthorAffiliation | InnoSyn B.V Patheon Regensburg GmbH Qpex Biopharma, Inc |
| AuthorAffiliation_xml | – name: Qpex Biopharma, Inc – name: InnoSyn B.V – name: Patheon Regensburg GmbH |
| Author_xml | – sequence: 1 givenname: Clemens surname: Stueckler fullname: Stueckler, Clemens – sequence: 2 givenname: Peter surname: Hermsen fullname: Hermsen, Peter organization: InnoSyn B.V – sequence: 3 givenname: Bas surname: Ritzen fullname: Ritzen, Bas organization: InnoSyn B.V – sequence: 4 givenname: Maria surname: Vasiloiu fullname: Vasiloiu, Maria – sequence: 5 givenname: Peter surname: Poechlauer fullname: Poechlauer, Peter – sequence: 6 givenname: Stefan surname: Steinhofer fullname: Steinhofer, Stefan – sequence: 7 givenname: Andreas surname: Pelz fullname: Pelz, Andreas – sequence: 8 givenname: Christopher surname: Zinganell fullname: Zinganell, Christopher – sequence: 9 givenname: Ulfried surname: Felfer fullname: Felfer, Ulfried – sequence: 10 givenname: Serge surname: Boyer fullname: Boyer, Serge organization: Qpex Biopharma, Inc – sequence: 11 givenname: Michel surname: Goldbach fullname: Goldbach, Michel organization: InnoSyn B.V – sequence: 12 givenname: André surname: de Vries fullname: de Vries, André organization: InnoSyn B.V – sequence: 13 givenname: Thomas surname: Pabst fullname: Pabst, Thomas organization: Patheon Regensburg GmbH – sequence: 14 givenname: Georg surname: Winkler fullname: Winkler, Georg organization: Patheon Regensburg GmbH – sequence: 15 givenname: Vito surname: LaVopa fullname: LaVopa, Vito – sequence: 16 givenname: Scott surname: Hecker fullname: Hecker, Scott organization: Qpex Biopharma, Inc – sequence: 17 givenname: Christian orcidid: 0000-0002-1404-2899 surname: Schuster fullname: Schuster, Christian email: christian.schuster@patheon.com |
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| Cites_doi | 10.1021/om50003a004 10.1002/adsc.201400747 10.1002/anie.197204731 10.1007/978-3-642-79709-5 10.1002/anie.196700411 10.1016/S0957-4166(97)00528-4 10.1021/acs.orglett.6b03753 10.1002/9783527689118.ch4 10.1021/acs.jmedchem.5b00127 10.1002/anie.196405131 10.1021/om50005a008 10.1021/jo4013942 10.1021/acs.oprd.7b00363 10.1002/047084289X.rd128 |
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| Keywords | Matteson reaction CSTR organolithium chemistry loop reactor α-chloro-boronate flow chemistry |
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| References | ref9/cit9 ref5/cit5c ref6/cit6 ref3/cit3 ref5/cit5a ref11/cit11 Matteson D. S. (ref5/cit5b) 1995 ref8/cit8a ref10/cit10a ref8/cit8c ref10/cit10b ref8/cit8b Poechlauer P. (ref1/cit1) 2017 ref2/cit2 ref4/cit4 ref7/cit7 |
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| Title | Development of a Continuous Flow Process for a Matteson Reaction: From Lab Scale to Full-Scale Production of a Pharmaceutical Intermediate |
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