758-12-3Relevant articles and documents
Kinetic understanding using NMR reaction profiling
Susanne, Flavien,Smith, David S.,Codina, Anna
, p. 61 - 64 (2012)
The combination of kinetic understanding and reaction modeling has been successfully applied to the development of processes from laboratory to manufacturing plant. Although extensively used in bulk chemistry, polymers, and the oil industry [ Bayer Technology Services, http://www.bayertechnology.cn/ uploads/media/0707-e-300dpi.pdf, July 2011; Lawrence Livermore National Laboratory, http://www1.eere.energy.gov/vehiclesandfuels/pdfs/merit-review-2011/ fuel-technologies/ft010-pitz-2 011-o.pdf,July 2011; Shin, S. B.; Han, S. P.; Lee, W. J.; Chae, J. H.; Lee, D. I.; Lee, W. H.; Urban, Z.Hydrocarbon Process. 2007, April) 83; Baumer, C.; Urban, Z.Hydrocarbon Process. 2007, June) 71 ], it has not been exploited to its full potential in the pharmaceutical industry. We present a fast and efficient methodology for kinetic modeling of chemical reactions using 1H NMR reaction monitoring that can be used for the process understanding and development of active pharmaceutical ingredients. The parameters that are important for the development of a good, reliable model for the prediction and optimization of reaction conditions are discussed. The hydrolysis of acetic anhydride was chosen to illustrate the methodology because it is mechanistically and kinetically well established.
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Lewis,Schutz
, p. 493 (1934)
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de la Mare,Dusouqui
, p. 251 (1967)
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Linschitz,Hobbs,Gross
, p. 3234 (1941)
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Tadokoro et al.
, p. 1504,1505 (1961)
Bonner
, p. 2661,2662 (1961)
Late-Stage β-C(sp3)-H Deuteration of Carboxylic Acids
Mal, Sourjya,Uttry, Alexander,Van Gemmeren, Manuel
supporting information, p. 10895 - 10901 (2021/08/03)
Carboxylic acids are highly abundant in bioactive molecules. In this study, we describe the late-stage β-C(sp3)-H deuteration of free carboxylic acids. On the basis of the finding that C-H activation with our catalysts is reversible, the de-deuteration process was first optimized. The resulting method uses ethylenediamine-based ligands and can be used to achieve the desired deuteration when using a deuterated solvent. The reported method allows for the functionalization of a wide range of free carboxylic acids with diverse substitution patterns, as well as the late-stage deuteration of bioactive molecules and related frameworks and enables the functionalization of nonactivated methylene β-C(sp3)-H bonds for the first time.
Production of Pure Aqueous13C-Hyperpolarized Acetate by Heterogeneous Parahydrogen-Induced Polarization
Kovtunov, Kirill V.,Barskiy, Danila A.,Shchepin, Roman V.,Salnikov, Oleg G.,Prosvirin, Igor P.,Bukhtiyarov, Andrey V.,Kovtunova, Larisa M.,Bukhtiyarov, Valerii I.,Koptyug, Igor V.,Chekmenev, Eduard Y.
supporting information, p. 16446 - 16449 (2016/11/09)
A supported metal catalyst was designed, characterized, and tested for aqueous phase heterogeneous hydrogenation of vinyl acetate with parahydrogen to produce13C-hyperpolarized ethyl acetate for potential biomedical applications. The Rh/TiO2catalyst with a metal loading of 23.2 wt % produced strongly hyperpolarized13C-enriched ethyl acetate-1-13C detected at 9.4 T. An approximately 14-fold13C signal enhancement was detected using circa 50 % parahydrogen gas without taking into account relaxation losses before and after polarization transfer by magnetic field cycling from nascent parahydrogen-derived protons to13C nuclei. This first observation of13C PHIP-hyperpolarized products over a supported metal catalyst in an aqueous medium opens up new possibilities for production of catalyst-free aqueous solutions of nontoxic hyperpolarized contrast agents for a wide range of biomolecules amenable to the parahydrogen induced polarization by side arm hydrogenation (PHIP-SAH) approach.
