Practical Synthesis of Chiral 3-(Hydroxyiminomethyl)adipic Acid, a Key Intermediate of the ROR-γ Inhibitor JTE-151, via Crystallization-Induced Dynamic Resolution
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Abstract
A practical six-step process for the production of chiral 3-(hydroxyiminomethyl)adipic acid 4 featuring highly efficient crystallization-induced dynamic resolution (CIDR) as the key step is reported. This compound was converted to isoxazole 23, an API starting material candidate of the ROR-γ inhibitor JTE-151, via isoxazole core construction by 1,3-dipolar cycloaddition and subsequent Ag2O-catalyzed decarboxylation of the tentatively introduced carboxyl group on the isoxazole core.
期刊介绍：
The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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