Practical Synthesis of Chiral 3-(Hydroxyiminomethyl)adipic Acid, a Key Intermediate of the ROR-γ Inhibitor JTE-151, via Crystallization-Induced Dynamic Resolution

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2023-11-20 DOI:10.1021/acs.oprd.3c00320

Hiromu Takiguchi*, Takashi Watanabe, Takashi Ogo, Hideaki Ishibashi, Katsuyuki Yokota, Shingo Obika and Takashi Inaba*,

引用次数: 0

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.

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结晶诱导动态分辨法合成ROR-γ抑制剂JTE-151关键中间体手性3-(羟亚胺甲基)己二酸

报道了一种以高效结晶诱导动态分辨(CIDR)为关键步骤的手性3-(羟亚胺甲基)己二酸4的六步法生产工艺。该化合物通过1,3-偶极环加成法构建异恶唑核，然后ag20催化异恶唑核上初步引入的羧基脱羧，转化为异恶唑23 (ROR-γ抑制剂JTE-151的API候选起始原料)。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

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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