A Novel and Practical Synthesis of Mavorixafor

IF 3.4 3区化学 Q1 Chemistry Organic Process Research & Development Pub Date : 2022-06-09 DOI:10.1021/acs.oprd.2c00076

Weiyuan Liu, Siju Bi, Ting Tian, Ting Zhou, Kuaile Lin and Weicheng Zhou*,

引用次数: 1

Abstract

A novel and practical synthesis of mavorixafor (1) is reported. The novelty of this synthetic route is the use of 8-chloro-5,6,7,8-tetrahydroquinoline (9) and 1,4-diaminobutane as the materials, instead of 8-amino-5,6,7,8-tetrahydroquinoline (4) and N,N-diprotected aminobutyraldehyde (6a or 6b). The preparation of (S)-8-(4-aminobutylamino)-5,6,7,8-tetrahydroquinoline (13) by resolution with N-acetyl-l-leucine was first achieved. Then the one-pot synthesis of 1 from 13 involving protection, condensation, and subsequent hydrolysis was successfully developed. In addition, the final product with a satisfactory purity (>99.5%, detected by both achiral and chiral HPLC) was obtained by a simple operation (salification) without column chromatographic purification.

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一种新颖实用的合成马佛里沙弗的方法

报道了一种新颖实用的合成马佛里沙福(1)的方法。该合成路线的新颖之处在于以8-氯-5,6,7,8-四氢喹啉(9)和1,4-二氨基丁烷为原料，代替了8-氨基-5,6,7,8-四氢喹啉(4)和N,N-二保护氨基丁醛(6a或6b)。首次用n -乙酰-l-亮氨酸拆分法制备了(S)-8-(4-氨基丁胺)-5,6,7,8-四氢喹啉(13)。然后，通过保护、缩合和随后的水解，成功地一锅合成了1。此外，无需柱层析纯化，通过简单的操作(盐化)获得了纯度满意的最终产品(>99.5%，非手性和手性HPLC均检测到)。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.50

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.