Synthesis of D,L-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

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Abstract

A method for the synthesis of 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, a racemic form of the antiparkinsonian drug levodopa and a biosynthetic precursor of melanins, has been developed. This amino acid is obtained in three steps with total yield of 59%, which exceeds previously published data. At the first step, the condensation of 3,4-dimethoxybenzaldehyde with benzoylglycine produced azlactone with 83% yield, followed by hydrolysis and reduction by Raney alloy in an alkaline solution, carried out in one step gave 3-(3,4-dimethoxyphenyl)-2-benzoylamineopropanoic acid with 90% yield. Further removal of the protective groups with hydrobromic acid followed by treatment with an aqueous ammonia solution resulted in 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid with 80% yield. The structure of all compounds obtained was confirmed by NMR and IR spectroscopy and elemental analysis. The X-ray diffraction analysis data of (Z)-2-benzamido-3-(3,4-dimethoxyphenyl)acrylic acid - an intermediate in the synthesis of DOPA has been provided for the first time in this paper.

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M. A. Barabanov

Postovsky Institute of Organic Synthesis UB RAS

Author for correspondence.
Email: flimsey@mail.ru
ORCID iD: 0000-0002-5850-8443
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22

G. S. Martyanov

Postovsky Institute of Organic Synthesis UB RAS

Email: flimsey@mail.ru
ORCID iD: 0009-0000-1152-0317
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22

M. I. Kodess

Postovsky Institute of Organic Synthesis UB RAS

Email: flimsey@mail.ru
ORCID iD: 0000-0003-4649-3659
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22

M. A. Ezhikova

Postovsky Institute of Organic Synthesis UB RAS

Email: flimsey@mail.ru
ORCID iD: 0000-0001-5689-5569
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22

P. A. Slepukhin

Postovsky Institute of Organic Synthesis UB RAS

Email: flimsey@mail.ru
ORCID iD: 0000-0001-8132-9905
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22

A. V. Pestov

Postovsky Institute of Organic Synthesis UB RAS; Ural Federal University

Email: flimsey@mail.ru
ORCID iD: 0000-0002-4270-3041
Russian Federation, 620108, Ekaterinburg, S. ul. Kovalevskoy, 22; 620002, Yekaterinburg, ul. Mira, 19

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2. Fig. 1. Z-3 acid in thermal ellipsoids of 50% probability according to X-ray diffraction data

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3. Fig. 2. Unit cell of the crystal of compound Z-3 (hydrogen atoms are not shown)

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4. Scheme 1

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