Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

doi:10.1055/S-2008-1032194

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Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

Published Mar 1, 2008 · A. Heim-Riether

Synthesis

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Abstract

Herein we describe an efficient and practical route for the regioselective synthesis of 4-(5-bromo/chloropyrazol-1-yl)-2-aminobutyric acids. The compounds have been prepared by regioselective C-5 halogenation of 1-(3,3-dimethoxypropyl)-1 H-pyrazole followed by a Strecker synthesis. In addition, Boc-protected 2-amino-4-(2-chlorophenyl)butyric acid and 2-amino-4-(3-chloropyridin-2-yl)butyric acid have been synthesized.

Study Snapshot

This study presents a practical route for the regioselective synthesis of 4-(5-bromo/chloropyrazol-1-yl)-2-aminobutyric acids, enabling the synthesis of 2-amino-4-(2-chlorophenyl)but

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

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References

Citations

N-Arylsulfonyl-α-amino carboxamides are potent and selective inhibitors of the chemokine receptor CCR10 that show efficacy in the murine DNFB model of contact hypersensitivity.

Eut-22 is a potent and selective inhibitor of CCR10, showing efficacy in the murine DNFB model of contact hypersensitivity, supporting its role in dermatological inflammatory conditions.

Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones.

This study developed a regioselective synthetic approach for preparing highly conjugated unnatural -amino acids with a 5-arylpyrazole side-chain, potentially useful for probes and fluorescent properties.

Replacing a stoichiometric silver oxidant with air: ligated Pd(II)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity

Air replaces toxic silver salt in Pd(II)-catalysis, resulting in improved chemoselectivity and diverse -aryl carbonyl derivatives without acid or base.

Synthesis and evaluation of tripeptidic plasmin inhibitors with nitrile as warhead

Nitrile-based peptidic plasmin inhibitors show potency against plasmin and selectivity against plasma kallikrein and urokinase, offering potential for treating diseases triggered by plasmin.

Ligated Regioselective PdII Catalysis to Access β‐Aryl‐Bearing Aldehydes, Ketones, and β‐Keto Esters

Ligated Regioselective PdII catalysis provides a milder and regioselective access to versatile -aryl aldehydes and ketones, enabling the synthesis of dihydrochalcones, -benzyl-′-al

One‐Pot Syntheses of α,β‐Unsaturated Carbonyl Compounds through Palladium‐Mediated Dehydrogenation of Ketones, Aldehydes, Esters, Lactones and Amides

Palladium-mediated dehydrogenation of ketones, aldehydes, esters, lactones, and amides can lead to,-unsaturated carbonyl compounds in one-pot synthesis.

Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

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References

Citations

N-Arylsulfonyl-α-amino carboxamides are potent and selective inhibitors of the chemokine receptor CCR10 that show efficacy in the murine DNFB model of contact hypersensitivity.

Eut-22 is a potent and selective inhibitor of CCR10, showing efficacy in the murine DNFB model of contact hypersensitivity, supporting its role in dermatological inflammatory conditions.

Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones.

This study developed a regioselective synthetic approach for preparing highly conjugated unnatural -amino acids with a 5-arylpyrazole side-chain, potentially useful for probes and fluorescent properties.

Replacing a stoichiometric silver oxidant with air: ligated Pd(II)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity

Air replaces toxic silver salt in Pd(II)-catalysis, resulting in improved chemoselectivity and diverse -aryl carbonyl derivatives without acid or base.

Synthesis and evaluation of tripeptidic plasmin inhibitors with nitrile as warhead

Nitrile-based peptidic plasmin inhibitors show potency against plasmin and selectivity against plasma kallikrein and urokinase, offering potential for treating diseases triggered by plasmin.

Ligated Regioselective PdII Catalysis to Access β‐Aryl‐Bearing Aldehydes, Ketones, and β‐Keto Esters

Ligated Regioselective PdII catalysis provides a milder and regioselective access to versatile -aryl aldehydes and ketones, enabling the synthesis of dihydrochalcones, -benzyl-′-al

One‐Pot Syntheses of α,β‐Unsaturated Carbonyl Compounds through Palladium‐Mediated Dehydrogenation of Ketones, ­Aldehydes, Esters, Lactones and Amides

Palladium-mediated dehydrogenation of ketones, aldehydes, esters, lactones, and amides can lead to,-unsaturated carbonyl compounds in one-pot synthesis.

One‐Pot Syntheses of α,β‐Unsaturated Carbonyl Compounds through Palladium‐Mediated Dehydrogenation of Ketones, Aldehydes, Esters, Lactones and Amides