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

M. A. Barabanov; Барабанов Михаил Александрович; G. S. Martyanov; Мартьянов Георгий Сергеевич; M. I. Kodess; Кодесс Михаил Исаакович; M. A. Ezhikova; Ежикова Марина Александровна; P. A. Slepukhin; Слепухин Павел Александрович; A. V. Pestov; Пестов Александр Викторович

doi:10.31857/S0514749224050137

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

Autores: Barabanov M.A.¹, Martyanov G.S.¹, Kodess M.I.¹, Ezhikova M.A.¹, Slepukhin P.A.¹, Pestov A.V.¹^,2
Afiliações:
1. Postovsky Institute of Organic Synthesis UB RAS
2. Ural Federal University
Edição: Volume 60, Nº 5 (2024)
Páginas: 688-698
Seção: Articles
URL: https://rjmseer.com/0514-7492/article/view/685349
DOI: https://doi.org/10.31857/S0514749224050137
EDN: https://elibrary.ru/RCJFNY
ID: 685349

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Resumo

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.

Palavras-chave

DOPA, dioxyphenylalanine, melanins, parkinsonism, azlacton, hydrogenation, Raney nickel

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