Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids

Jászay, Zsuzsa M.; Petneházy, Imre; Tőke, Lásʐló

doi:10.1055/s-1989-27380

Cited by 30 publications

(14 citation statements)

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“…To explore the formation of acid tosylate during the reaction, a mixture of benzoic acid, tosyl chloride was reacted with 1-methylimidazole at 60 °C. TLC monitoring indicated the formation of tosyl benzoate as identified with an authentic sample [37]. Moreover, no benzoic anhydride was observed.…”

Section: Resultsmentioning

confidence: 79%

Efficient method for the direct preparation of aryl carboxylates from carboxylic acids using tosyl chloride under solvent-free conditions

Khalafi-Nezhad

Parhami

Zare

2008

JICS

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A simple, clean and efficient solvent-free procedure for the preparation of aryl carboxylates is described from the direct reaction of carboxylic acids and phenols, in the presence of 1-methylimidazole as base and tosyl chloride (TsCl) as coupling agent. This method can be easily applied for different substituted phenols and carboxylic acids. It can also be applied for the selective acylation when other functional group such as hydroxyl is present on phenol ring.

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Section: Resultsmentioning

confidence: 79%

Efficient method for the direct preparation of aryl carboxylates from carboxylic acids using tosyl chloride under solvent-free conditions

Khalafi-Nezhad

Parhami

Zare

2008

JICS

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“…Several acyl chlorides and sulfonyl chlorides , were investigated. Considering that anhydride intermediates were not stable enough for thorough characterization, 4-nitrophenethylamine 15 was used to capture the anhydride intermediates.…”

Section: Results and Discussionmentioning

confidence: 99%

Concise Synthesis of Key Intermediate of Mirabegron via a Mixed Anhydride Method

Zhang

Zhuang

Liu

et al. 2016

Org. Process Res. Dev.

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An efficiently scalable synthesis of key intermediate toward mirabegron has been developed via a mixed anhydride method, employing PivCl instead of EDCI and HOBt. The developed process produced (R)-2-hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide (10) in 91.5–92.3% yield and >99.0% HPLC purity under mild conditions. During this process, a side reaction induced by triethylamine hydrochloride was discovered and investigated, which was ultimately avoided by executing the reaction in a biphasic solvent system.

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“…Aside from demonstrating the generality of this new one-pot protocol, we have accumulated spectroscopic evidence which directly proves the existence of acyl mesylates for the first time. We have also reinvestigated some previous reports which claimed to employ acyl mesylates and have determined that, in most cases, symmetrical anhydrides are the actual intermediates present as a result of sulfonyl chloride-mediated dehydration.…”

mentioning

confidence: 77%

“…The current method takes advantage of the highly reactive nature of the acyl mesylate species in order to activate sterically hindered acids for attack by diazomethane. Although a few scattered reports on the use of acyl mesylates are present in the literature, there is no definitive evidence that the intermediates of these reactions are actually acyl mesylates 4c. Aside from demonstrating the generality of this new one-pot protocol, we have accumulated spectroscopic evidence which directly proves the existence of acyl mesylates for the first time.…”

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confidence: 90%

New Synthetic Technology for the Synthesis of Hindered α-Diazoketones via Acyl Mesylates

et al. 1999

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[formula: see text] A mild and reliable one-pot protocol for the elaboration of sterically demanding carboxylic acids into alpha-diazoketones via acyl mesylates has been developed. Aside from delineating the reaction parameters which render this strategy quite general for hindered carboxylic acids, we have directly proven the existence of the fleeting acyl mesylate group as the reactive species in these reactions and shed light onto the differing mechanisms which are operative in the activation of hindered and simple carboxylic acids with methanesulfonyl chloride.

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Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids

Cited by 30 publications

References 0 publications

Efficient method for the direct preparation of aryl carboxylates from carboxylic acids using tosyl chloride under solvent-free conditions

Efficient method for the direct preparation of aryl carboxylates from carboxylic acids using tosyl chloride under solvent-free conditions

Concise Synthesis of Key Intermediate of Mirabegron via a Mixed Anhydride Method

New Synthetic Technology for the Synthesis of Hindered α-Diazoketones via Acyl Mesylates

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