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Methyl 2-[(tert-Butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate: Synthesis of Erythro (±) Isomer by Reduction and Threo (±) Isomer by Inversion Method

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Abstract

We report an efficient protocol for synthesis of methyl 2-[(tert-butoxycarbonyl) amino]-3-hydroxy-3-phenylpropanoate (Erythro (±)) by simple reduction and methyl 2-[(tert-butoxycarbonyl) amino]-3-hydroxy-3-phenylpropanoate (Threo (±)) by inversion method. The erythro (±) isomer has been obtained in excellent yield (93%) using sodium borohydride in methanol at -40°C. The erythro isomer has been effectively converted into its threo (±) with 100% efficiency, by inversion, using methanesulfonyl chloride, cesium acetate and crown ether-18-6. The salient features of this method include cost effectiveness, excellent yields and scope for large-scale synthesis, which makes the method an attractive addition to the applicable methodologies.

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REFERENCES

  1. Oikawa, M.S., and Kusumoto, S., Tetrahedron: Asymmetry, 1995, vol. 6, p. 961. https://doi.org/10.1016/0957-4166(95)00106-Y

  2. Serbia, F., Chammaa, S., Ruiz, A.S., Ortiz, L.M., and Herrera, F.L., Curr. Med. Chem., 2004, vol. 11, p. 1309. https://doi.org/10.2174/0929867043365224

  3. Hamada, Y., Shioiri, T., Chem. Rev., 2005, vol. 105, pp. 4441–4482. https://doi.org/10.1021/cr0406312

    Article  CAS  PubMed  Google Scholar 

  4. Tian, H., Jiao, X., Xie, P., and Liang, X., Tetrahedron Lett., 2005, vol. 46, p. 8579. https://doi.org/10.1016/j.tetlet.2005.09.188

  5. Yurek-George, A., Habens, F., Brimmell, M., Packham, M., and Ganesan, A., J. Am. Chem. Soc., 2004, vol. 126, p. 1030. https://doi.org/10.1021/ja039258q

  6. Mordant, C., Reymond, C., Tone, H., Lavergne, D., Touati, R., Hassine, B.B., Vidal, V.R., and Genet, J.P., Tetrahedron., 2007, vol. 63, p. 6115. https://doi.org/10.1016/j.tet.2007.03.036

  7. Alemany, C., Bach, J., Garcia, J., Lopez, M., and Rodriguez, A.B., Tetrahedron., 2000, vol. 56, p. 9305. https://doi.org/10.1016/S0040-4020(00)00905-4

  8. Lohray, B., Reddy, A., and Bhushan, S.V., Tetrahedron: Asymmetry, 1996, vol. 7, p. 2411. https://doi.org/10.1016/0957-4166(96)00299-6

  9. Seebach, D., and Fritz, M.G., Int. J. Biol. Macromol., 1999, vol. 25, p. 217. https://doi.org/10.1016/S0141-8130(99)00037-9

  10. Reddy, C.S.K., Ghai, R., Rashmi, K., and Kalia, V.C., Bioresour. Technol., 2003, vol. 87, p. 137. https://doi.org/10.1016/S0960-8524(02)00212-2

  11. Ren, O., Ruth, K., Thony-Meyer, L., and Zinn, M., Appl. Microbial. Biotechnol., 2010, vol. 87, p. 41. https://doi.org/10.1007/s00253-010-2530-6

  12. Jarvis, A.P., Schaaf, O., and Oldham, N.J., Planta, 2000, vol. 212, p. 119126. https://doi.org/10.1007/s004250000377

    Article  Google Scholar 

  13. Burlingame, R., and Chapman, P.J., J. Bacterial., 1983, vol. 155, p. 113. https://doi.org/10.1128/jb.155.1.113-121.1983

  14. Bahre, F., and Maier, H.G., Deut. Lebens., 1999, vol. 95, p. 399.

  15. Rizzo, C., Bertini, E., Piemonte, F., Leuzzi, V., Sabetta, G., Federici, G., Luchetti, A., and DionisiVici, C.J., J. Inherit, Metab. Dis., 2000, vol. 23, p. 349. https://doi.org/10.1023/a:1005675012708

  16. Watkins, F.B., Chittiboyina, A.G., and Avery, M.A., Eur. J. Org. Chem., 2006, vol. 2006, p. 4071. https://doi.org/10.1002/ejoc.200600149

  17. Nagamitsu, T., Takano, D., Fukuda, T., Otoguro, K., Kuwajima, I., Harigaya, Y., and Omura, S., Org. Lett., 2004, vol. 6, p. 1865. https://doi.org/10.1021/jo062089i

  18. Brinton, S.L., Piret, V., Christine, H., and Peter, S., Org. Lett., 2010 vols. 12, p. 5274. https://doi.org/10.1021/ol102323k

  19. Okiko, M., Hiroshi, A., and Takeaki, N., Chem. Pharm. Bull., 2005, vol. 53, vol. 355. https://doi.org/10.1248/cpb.53.355

  20. Quentin, L., Gerard, G., Phannarath, P., and Virginie, R.V., Org. Lett., 2017, vol. 19, p. 6428. https://doi.org/10.1021/acs.orglett.7b03332

  21. Shigeki, M., Naoya, K., Shinji, H., and Katsu, S.M., J. Am. Chem. Soc., 2003, vol. 125, p. 4712. https://doi.org/10.1021/ja034787f

  22. Bhatia, S., Singh, S., Kumar, R., Kumar, A., Olsen, C.E., and Prasad, A.K., Indian J. Chem., 2013, vol. 52B, p. 379.

    Google Scholar 

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ACKNOWLEDGMENTS

Mrs. Vijaya Lakshmi Chapala is thankful to GITAM deemed to be University, Hyderabad for providing the laboratory facilities.

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Authors and Affiliations

  1. Department of Chemistry, School of Science, GITAM deemed to be University, 502329, Hyderabad, India

    Vijaya Lakshmi C, Naresh Kumar Katari & Giri Prasad M

  2. School of Chemistry and Physics, College of Agriculture, Engineering and Science, Westville Campus, University of KwaZulu-Natal, P Bag X 54001, 4000, Durban, South Africa

    Naresh Kumar Katari & Sreekantha B. Jonnalagadda

  3. Analytical R&D, Hikma Pharmaceuticals USA Inc, Columbus, 43228, Ohio, USA

    Vijay Kumar Rekulapally

  4. Department of Chemistry, GITAM School of Science, GITAM deemed to be University, 562163, Bengaluru, India

    Nagaraju Kerru

Authors
  1. Vijaya Lakshmi C
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  2. Naresh Kumar Katari
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  3. Giri Prasad M
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  4. Nagaraju Kerru
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  5. Vijay Kumar Rekulapally
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  6. Sreekantha B. Jonnalagadda
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Correspondence to Naresh Kumar Katari or Sreekantha B. Jonnalagadda.

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C, V.L., Katari, N.K., M, G.P. et al. Methyl 2-[(tert-Butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate: Synthesis of Erythro (±) Isomer by Reduction and Threo (±) Isomer by Inversion Method. Russ J Gen Chem 91, 2539–2545 (2021). https://doi.org/10.1134/S1070363221120252

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