Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate

Bisenieks, Egils; Poikans, Janis; Plotniece, Aiva; Bernotiene, Eiva; Tsai, Wei-Bor; Sobolev, Arkadij

doi:10.3390/M1148

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Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate

by

Egils Bisenieks

¹,

Janis Poikans

¹,

Aiva Plotniece

¹

,

Eiva Bernotiene

²,

Wei-Bor Tsai

³

and

Arkadij Sobolev

^1,*

¹

Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga LV-1006, Latvia

²

State Research Institute Centre for Innovative Medicine, Santariskiu 5, LT-08406 Vilnius, Lithuania

³

Department of Chemical Engineering, National Taiwan University, No.1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan

^*

Author to whom correspondence should be addressed.

Molbank 2020, 2020(3), M1148; https://doi.org/10.3390/M1148

Submission received: 19 May 2020 / Revised: 2 July 2020 / Accepted: 11 July 2020 / Published: 14 July 2020

(This article belongs to the Collection Heterocycle Reactions)

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Abstract

The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due to their broad range of biological activities. Herein, the formation of amide bond between 1,4-dihydroisonicotinic acid and l-methionine is reported. The coupling of l-methionine with pentafluorophenyl active ester of 1,4-dihydroisonicotinic acid appears to be a convenient and effective method for amide bond formation. Sodium N-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate has been successfully synthesized via a procedure where the key step is amide formation from 5-diethyl 4-(perfluorophenyl) 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylate and l-methionine. Sodium salt formation was performed to improve physicochemical properties, such as solubility of the l-methionine-derived 1,4-dihydroisonicotinamide. The obtained target compound was fully characterized by UV, IR, ¹H NMR, ¹³C NMR, MS, and microanalysis.

Keywords: 1,4-dihydropyridine; 1,4-dihydroisonicotinic acid; l-methionine

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MDPI and ACS Style

Bisenieks, E.; Poikans, J.; Plotniece, A.; Bernotiene, E.; Tsai, W.-B.; Sobolev, A. Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate. Molbank 2020, 2020, M1148. https://doi.org/10.3390/M1148

AMA Style

Bisenieks E, Poikans J, Plotniece A, Bernotiene E, Tsai W-B, Sobolev A. Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate. Molbank. 2020; 2020(3):M1148. https://doi.org/10.3390/M1148

Chicago/Turabian Style

Bisenieks, Egils, Janis Poikans, Aiva Plotniece, Eiva Bernotiene, Wei-Bor Tsai, and Arkadij Sobolev. 2020. "Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate" Molbank 2020, no. 3: M1148. https://doi.org/10.3390/M1148

APA Style

Bisenieks, E., Poikans, J., Plotniece, A., Bernotiene, E., Tsai, W.-B., & Sobolev, A. (2020). Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate. Molbank, 2020(3), M1148. https://doi.org/10.3390/M1148

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Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate

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