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Synthesis of Glycyl-(S)-5-hydroxynorvaline

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Abstract

The dipeptide glycyl-(S)-5-hydroxynorvaline was obtained from 1-tert-butyl 5-methyl N-Boc-glycyl-(S)-glutamate via saponification, reduction of the activated 5-carboxy group with sodium borohydride, removal of the N-Boc and OBut protecting groups by refluxing in aqueous dioxane. Using the example of the synthesis of (S)-5-hydroxynorvaline, it was shown that the used sequence of chemical transformations is not accompanied by racemization.

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Fig. 1.
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ACKNOWLEDGMENTS

The work was carried out using the equipment of the Center for Collective Use "Spectroscopy and Analysis of Organic Compounds" at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch).

Funding

The work was financially supported by the Russian Science Foundation (project no. 19-13-00231-P).

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Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620108, Yekaterinburg, Russia

    E. N. Chulakov, A. A. Tumashov, D. A. Gruzdev, G. L. Levit & V. P. Krasnov

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  1. E. N. Chulakov
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  2. A. A. Tumashov
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  3. D. A. Gruzdev
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  4. G. L. Levit
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  5. V. P. Krasnov
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Correspondence to E. N. Chulakov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1507–1512 https://doi.org/10.31857/S0514749223110149.

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Chulakov, E.N., Tumashov, A.A., Gruzdev, D.A. et al. Synthesis of Glycyl-(S)-5-hydroxynorvaline. Russ J Org Chem 59, 2003–2007 (2023). https://doi.org/10.1134/S1070428023110222

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  • DOI: https://doi.org/10.1134/S1070428023110222

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