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Synthesis of N-carboxyalkyl-1,4-benzothiazepine-3(2H)-one derivatives using esters of N-(2-chloro-5-nitrobenzyl)amino acids

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Abstract

Two alternative approaches for synthesis of esters of N-(2-chloro-5-nitrobenzyl) amino acids have been developed and compared. We have found synthesis of N-(2-chloro-5-nitrobenzyl) amino acids via alkylation of esters of amino acids in DMF in the presence of Et3N and NaI to be more convenient and have higher yields in comparison with reduction of Schiff bases obtained from 2-chloro-5-nitrobenzaldehyde and corresponding esters of amino acids by NaBH4. Treatment of the solutions of esters of N-(2-chloro-5-nitrobenzyl) amino acids in DMSO with methyl thioglycolate and following intramolecular acylation in xylene led to N-carboxyalkyl-1,4-benzothiazepine-3(2H)-one derivatives in 24–76 % yields.

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Authors and Affiliations

  1. Department of Organic Chemistry, Taras Shevchenko Kyiv National University, 64 Volodymyrska str., 01033, Kyiv, Ukraine

    Taras M. Tarasiuk, Tetiana A. Volovnenko & Yulian M. Volovenko

  2. STC “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Lenina ave., 61001, Kharkiv, Ukraine

    Volodymyr V. Medviediev & Oleg V. Shishkin

  3. Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., 61122, Kharkiv, Ukraine

    Oleg V. Shishkin

Authors
  1. Taras M. Tarasiuk
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  2. Tetiana A. Volovnenko
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  3. Yulian M. Volovenko
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  4. Volodymyr V. Medviediev
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  5. Oleg V. Shishkin
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Correspondence to Taras M. Tarasiuk.

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Tarasiuk, T.M., Volovnenko, T.A., Volovenko, Y.M. et al. Synthesis of N-carboxyalkyl-1,4-benzothiazepine-3(2H)-one derivatives using esters of N-(2-chloro-5-nitrobenzyl)amino acids. Monatsh Chem 145, 483–489 (2014). https://doi.org/10.1007/s00706-013-1133-1

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  • DOI: https://doi.org/10.1007/s00706-013-1133-1

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