Supercritical fluid chromatography for GMP analysis in support of pharmaceutical development and manufacturing activities

Hicks, Michael B.; Regalado, Erik L.; Tan, Feng; Gong, Xiaoyi; Welch, Christopher J.

doi:10.1016/j.jpba.2015.09.014

Cited by 48 publications

(5 citation statements)

References 23 publications

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“…The toluene solvent and the intermediate imine formed upon hydroamination could be vacuum transferred away from the titanium catalyst and into a clean reaction vessel. Complex 2 and all other reagents for ATH were then added, and upon reaction completion 7h was obtained in 90% ee (average ee after the experiment was performed in triplicate) in contrast to the one-pot procedure where 7h was yielded with >99% ee (Table , entry 8), indicating that indeed the presence of the titanium catalyst has a notable impact …”

Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights To Realize the Enantioselective Synthesis of Piperazines

2016

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An efficient and practical catalytic approach for the enantioselective synthesis of 3-substituted morpholines through a tandem sequential one-pot reaction employing both hydroamination and asymmetric transfer hydrogenation reactions is described. Starting from ether-containing aminoalkyne substrates, a commercially available bis(amidate)bis(amido)Ti catalyst is utilized to yield a cyclic imine that is subsequently reduced using the Noyori-Ikariya catalyst, RuCl [(S,S)-Ts-DPEN] (η-p-cymene), to afford chiral 3-substituted morpholines in good yield and enantiomeric excesses of >95%. A wide range of functional groups is tolerated. Substrate scope investigations suggest that hydrogen-bonding interactions between the oxygen in the backbone of the ether-containing substrate and the [(S,S)-Ts-DPEN] ligand of the Ru catalyst are crucial for obtaining high ee's. This insight led to a mechanistic proposal that predicts the observed absolute stereochemistry. Most importantly, this mechanistic insight allowed for the extension of this strategy to include N as an alternative hydrogen bond acceptor that could be incorporated into the substrate. Thus, the catalytic, enantioselective synthesis of 3-substituted piperazines is also demonstrated.

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Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights To Realize the Enantioselective Synthesis of Piperazines

2016

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“…Since the resurgence of SFC in the beginning of the 2010s and the launch of new instrumentations, several studies were performed to demonstrate the quantitative performance of this technique [72]. Firstly, the technical improvements of new SFC instruments were clearly highlighted as beneficial to improve UV sensitivity, injection reproducibility and method robustness [73]. More recently, SFC-MS/MS was proposed as an alternative technique for nitrosamine analysis [74].…”

Section: Quantitative Performance Of Sfcmentioning

confidence: 99%

Application space for SFC in pharmaceutical drug discovery and development

Losacco

Dispas

Veuthey

et al. 2022

Separation Science and Technology

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“…Improved peak shape, resolution, and analysis time were a significant driver underlying this expansion of SFC., 110 As the SFC is subject to continuous development, both by upgrades of instrumentation as well as by expanding selection of commercially available columns, the automated enantioselective SFC method development evolved from run times of more than half hour to current speed of just few minutes. 49 , 110 , 111 , 112 …”

Section: Other Studiesmentioning

confidence: 99%

Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Folprechtová

Kalíková

2020

Analytical Science Advances

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Increasing number of reported works dealing with macrocyclic glycopeptide‐based columns in sub/supercritical fluid chromatography (SFC) points to the growing interest in this area. With the development and production of sub 2 µm fully porous particles and superficially porous particles with bonded macrocyclic glycopeptides, significant improvements have been made in ultrafast high efficiency chiral SFC. This review article gives an overview of macrocyclic glycopeptide‐based chiral selectors that were used in theoretical studies and/or applications in SFC. The review covers the period from 1997 when macrocyclic glycopeptides were first used in SFC till the end of July 2020 according to Web of Science. This work can also be helpful to analysts searching for an appropriate method for the separation/determination of enantiomers of their interest.

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Supercritical fluid chromatography for GMP analysis in support of pharmaceutical development and manufacturing activities

Cited by 48 publications

References 23 publications

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights To Realize the Enantioselective Synthesis of Piperazines

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights To Realize the Enantioselective Synthesis of Piperazines

Application space for SFC in pharmaceutical drug discovery and development

Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

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