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Synthesis of (3S,4S)-4-Acetyl-3-(1R)-1-hydroxyethyl-1-(4-methoxyphenyl)azetidin-2-one

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Abstract

The synthesis of the title compound from l-threonine with the participation of β-methallyl chloride amide in the N-alkylation step is described.

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REFERENCES

  1. Grzeszczyk, B., Stecko, S., Mucha, Ł., Staszewska-Krajewska, O., Chmielewski, M., and Furman, B., J. Antibiot., 2013, vol. 66, p. 161. https://doi.org/10.1038/ja.2013.8

    Article  CAS  Google Scholar 

  2. Berks, A.H., Tetrahedron, 1996, vol. 52, p. 331. https://doi.org/10.1016/0040-4020(95)00842-X

    Article  CAS  Google Scholar 

  3. Worthington, R.J. and Melander, C., J. Org. Chem., 2013, vol. 78, p. 4207. https://doi.org/10.1021/jo400236f

    Article  CAS  Google Scholar 

  4. Xu, J., Tetrahedron, 2012, vol. 68, p. 10696. https://doi.org/10.1016/j.tet.2012.04.007

    Article  CAS  Google Scholar 

  5. Fu, N. and Tidwell, T.T., Tetrahedron, 2008, vol. 64, p. 10465. https://doi.org/10.1016/S0040-4020(01)96429-4

    Article  CAS  Google Scholar 

  6. Stecko, S., Furman, B., and Chmielewski, M., Tetrahedron, 2014, vol. 70, p. 7817. https://doi.org/10.1016/j.tet.2014.06.024

    Article  CAS  Google Scholar 

  7. Wannenmacher, N., Pfeffer, C., Frey, W., and Peters, R., J. Org. Chem., 2022, vol. 87, p. 670. https://doi.org/10.1021/acs.joc.1c02640

    Article  CAS  Google Scholar 

  8. Yamamoto, Y., Kodama, Sh., Nishimura, R., Nomoto, A., Ueshima, M., and Ogawa, A., J. Org. Chem., 2021, vol. 86, p. 11571. https://doi.org/10.1021/acs.joc.1c01128

    Article  CAS  Google Scholar 

  9. Hosseini, A. and Schreiner, P.R., Org. Lett., 2019, vol. 21, p. 3746. https://doi.org/10.1021/acs.orglett.9b01192

    Article  CAS  Google Scholar 

  10. Laurent, M., Cérésiat, M., and Marchand-Brynaert, J., Eur. J. Org. Chem., 2006, vol. 16, p. 3755. https://doi.org/10.1002/ejoc.200600235

    Article  CAS  Google Scholar 

  11. Selezneva, N.K. Valiullina, Z.R., Khasanova, L.S., Gimalova, F.A., Biglova, R.Z., and Miftakhov, M.S., Mendeleev Commun., 2018, vol. 28, p. 131. https://doi.org/10.1016/j.mencom.2018.03.005

    Article  CAS  Google Scholar 

  12. Shimohigashi, Y., Waki, M., and Nobuo, I., Bull. Chem. Soc. Jpn, 1979, vol. 52, p. 949. https://doi.org/10.1246/bcsj.52.949

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

Analyses were performed on the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Russian Academy of Sciences.

Funding

The work was performed according to the state assignment no. 122031400261-4.

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Correspondence to A. M. Galeeva.

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The authors declare no conflict of interest.

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Selezneva, N.K., Galeeva, A.M., Valiullina, Z.R. et al. Synthesis of (3S,4S)-4-Acetyl-3-(1R)-1-hydroxyethyl-1-(4-methoxyphenyl)azetidin-2-one. Russ J Org Chem 58, 1676–1679 (2022). https://doi.org/10.1134/S1070428022110203

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