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(S)-Ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate

Department of Pharmacy - Pharmaceutical Sciences, University of Bari, Via E. Orabona 4, 70126 Bari, Italy
Authors to whom correspondence should be addressed.
Molbank 2019, 2019(1), M1049;
Received: 18 January 2019 / Revised: 15 February 2019 / Accepted: 18 February 2019 / Published: 21 February 2019
(This article belongs to the Section Organic Synthesis)
PDF [764 KB, uploaded 21 February 2019]


A multistep gram-scale synthesis of (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate (2) has been developed. The title compound was prepared starting from commercially available l-DOPA which was O- and N-protected before undergoing iodination by CF3CO2Ag/I2. The structure of the target compound was confirmed using IR, 1H-NMR, 13C-NMR, 2D (COSY, HSQC) NMR spectroscopy, as well as ESI-MS and HRMS. View Full-Text
Keywords: phenylalanine; l-DOPA; iodination; medicinal chemistry phenylalanine; l-DOPA; iodination; medicinal chemistry

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Lentini, G.; Cavalluzzi, M.M.; Degennaro, L.; Fracchiolla, G.; Perna, F.; Scilimati, A. (S)-Ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate. Molbank 2019, 2019, M1049.

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