合成和开发用于大规模制备 3-去氧吗啡的非烷基酯

IF 0.7 4区化学 Q4 CHEMISTRY, ORGANIC

Letters in Organic Chemistry Pub Date : 2024-01-22 DOI:10.2174/0115701786284466240105074539

Antonio M. Ruda, Jonathan D. Moseley

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引用次数: 0

摘要

:我们合成了一系列新型吗啡活化酯，作为三酯的替代品，并将其置于氢解条件下。其中，只有新型非三酸酯可以完全转化为有用的中间体--3-脱氧吗啡。这种转化的速度明显快于三酸酯，而且合成中间体壬酸酯的成本也大大降低，这对于在药物开发项目中大规模制备 3-去氧吗啡来说是一个重要因素。

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Synthesis and Development of a Nonaflate Ester in the Large-Scale Preparation of 3-Deoxymorphine

: A series of novel activated esters of morphine were synthesized as alternatives to the triflate ester and submitted to hydrogenolysis conditions. Of these, only the novel nonaflate ester could be transformed with full conversion into the useful intermediate, 3-deoxymorphine, which was isolated in good yield and high purity without chromatography. This conversion proceeded significantly faster than for the triflate ester and with synthesis of the intermediate nonaflate at much reduced cost, an important factor for the large-scale preparation of 3-deoxymorphine in drug development projects.

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来源期刊

Letters in Organic Chemistry 化学-有机化学

CiteScore

1.30

自引率

12.50%

发文量

135

审稿时长

7 months

期刊介绍： Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.