Oxidative decarboxylation of arylacetic acids and arylacetic esters with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

Najminejad, Z

doi:10.1007/s12039-023-02243-5

J Chem Sci

2024

DOI: 10.1007/s12039-023-02243-5

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Oxidative decarboxylation of arylacetic acids and arylacetic esters with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

Z Najminejad

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2024

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Cited by 2 publications

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High‐Throughput Experimentation (HTE) Applied to the Synthesis of API Impurities: A Case Study in Oxidative Decarboxylation of Aryl Acetic Acids

Paolo,

Martínez Fornaso,

Elhalem

et al. 2024

Eur J Org Chem

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High‐throughput experimentation (HTE) has dramatically impacted experimental reaction development by enabling the rapid exploration of a diverse set of reaction conditions. During the past few decades, HTE has evolved as a tool to expedite reaction discovery and optimization. This work details the application of HTE to synthesize impurities of active pharmaceutical ingredients (APIs) with ketone/aldehyde functionality, specially focusing on ibuprofen impurity E. Initial experiments using K2S2O8 as oxidant yielded moderate results. Subsequent HTE screens identified cerium ammonium nitrate (CAN) and RuCl3‐NaIO4 as new effective decarboxylative oxidants, with RuCl3‐NaIO4 in the presence of tetrabutylammonium bromide (TBAB) achieving the highest yield of 65%. This optimized method was successfully applied to synthesize ibuprofen impurity E on a gram scale. Additionally, the applicability of these methods to obtain other API related substances, such as naproxen impurity L and ketoprofen impurity A, was demonstrated. This research highlights the potential of HTE to streamline the synthesis of API impurities, making them widely accessible for pharmaceutical development purposes.

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High‐Throughput Experimentation (HTE) Applied to the Synthesis of API Impurities: A Case Study in Oxidative Decarboxylation of Aryl Acetic Acids

Paolo,

Martínez Fornaso,

Elhalem

et al. 2024

Eur J Org Chem

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Convenient transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

Najminejad

2024

Journal of Sulfur Chemistry

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Oxidative decarboxylation of arylacetic acids and arylacetic esters with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

Cited by 2 publications

References 63 publications

High‐Throughput Experimentation (HTE) Applied to the Synthesis of API Impurities: A Case Study in Oxidative Decarboxylation of Aryl Acetic Acids

High‐Throughput Experimentation (HTE) Applied to the Synthesis of API Impurities: A Case Study in Oxidative Decarboxylation of Aryl Acetic Acids

Convenient transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

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