SYNTHESIS OF ANALOG L-α-METIL-DOPA FROM EUGENOL

https://doi.org/10.22146/ijc.21788

Hanoch J Sohilait(1*), Hardjono Sastrohamidjojo(2), Sabirin Matsjeh(3), J Stuart Grossert(4)

(1) epartment of Chemistry, Faculty of Mathematics and Natural Sciences Pattimura University, Kampus PGSD, Ambon
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara Yogyakarta
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara Yogyakarta
(4) epartment of Chemistry, Dalhousie University Nova Scotia, Canada
(*) Corresponding Author

Abstract


Synthesis of analog L-α-metil-Dopa from eugenol has been achieved through conversion of allyl group to ketone, followed by reaction with NH3 and KCN and by hydrolisis. The addition reaction of methyleugenol with formic acid yield methyleugenyl formate (60,69%). The hydrolis of methyileugenylformate with KOH in aqaueous-ethanolic solution produced methyleugenyl alcohol (73,68%). The oxidation of methyleugenyl alcohol with PCC yield methyleugenyl ketone (67,71%). The reaction of methyleugenyl ketone with NH3 and KCN yield D,L-α-amino-α-(3,4-dimetoxybenzyl) propionitril (84,14%). The hydrolisis of D,L-α-amino-α-(3,4-dimetoxybenzyl) propionitril with concentrated hydrochloric acid gave Analog L-α-metil-Dopa as a main target (91,98%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS



Keywords


Analog L-α-metil-Dopa; eugenol

Full Text:

Full Text PDF


References

[1] Reinhold, D.F., Firestone, R.A., Gaines, W.A., Chemerda, J.M., and Sletzingers, M., 1968, J. Org. Chem., Vol.33, 1209-1213.

[2] Fuhrhop, J., Penzlin, G., 1994, Organic Synthesis, Concepts, Methods, Starting Material, second edition, VCH Weinheim, 50.

[3] Sittig, M., 1979, Pharmaceutical Manufacturing Encyclopedia, Noyes Data Corporation, Park Ridge

[4] Anwar, C., 1994, The Conversion of Eugenol into More Valuable Substances, Desertation, Universitas Gadjah Mada, Yogyakarta.

[5] Sohilait, H.J., 2003; Sigma, 6, 2, 193-196.

[6] Sohilait, H.J., Sastrohamidjojo, H., Matsjeh, S., and Grossert, J.St., 2001, Indo. J. Chem., 1, 3, 145-148



DOI: https://doi.org/10.22146/ijc.21788

Article Metrics

Abstract views : 2358 | views : 2940


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.