Alternative Routes in Cesium Carbonate-Promoted Reactions of tert-Butyl n-(Diphenylmethylene)Glycinate with 2-Methyl-3-{[tert-Butyl(Dimethyl)Silyl]Oxy}Propanoic and Acetic Acid Chlorides

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Abstract

It was shown that the reaction of tert-butyl N-(diphenylmethylene)glycinate with 2-methyl-3-{[tert-butyl(dimethyl)silyl]oxy}propanoic acid chloride in CH2Cl2 in the presence of Cs2CO3 proceeds with the formation of the corresponding β-lactam and an acetylglycine derivative. Under the same conditions, acetyl chloride reacts with tert-butyl N-(diphenylmethylene)glycinate chemoselectively, yielding exclusively tert-butyl ester of acetylglycine.

About the authors

Z. R Valiullina

Ufa Institute of Chemistry UFRC RAS

Email: valiullina.zulya@mail.ru
ORCID iD: 0000-0002-6868-4870
Ufa, Russia

G. R Sunagatullina

Ufa Institute of Chemistry UFRC RAS

ORCID iD: 0000-0002-2691-1801
Ufa, Russia

M. S Miftakhov

Ufa Institute of Chemistry UFRC RAS; Academy of Sciences of the Republic of Bashkortostan

ORCID iD: 0000-0002-0269-7484
Ufa, Russia; Ufa, Russia

References

  1. Nicolau D.P. Expert Opin. Pharmacother. 2008, 9, 23–37. https://doi.org/10.1517/14656566.9.1.23
  2. El-Gamal M.I., Brahim I., Hisham N. Aladdin R., Mohammed H., Bahaaeldin A. Eur. J. Med. Chem. 2017, 131, 185–195. https://doi.org/10.1016/J.EJMECH.2017.03.022
  3. Meng K., Shim P., Wang Q., Zhao S., Gu T., Kahsai F.W., Ahn S., Chen X. Bioorg. Med. Chem. 2018, 26, 2320–2330. https://doi.org/10.1016/j.bmc.2018.03.023
  4. Shirakawa S., Maruoka K. Angew. Chem. Int. Ed. 2013, 52, 4312–4348. https://doi.org/10.1002/anie.201206835
  5. Prathibha E., Rangasamy R., Sridhar A., Lakshmi K. Chemistry Select. 2020, 5, 988–993. https://doi.org/10.1002/slct.201903706
  6. O'Donnell M.J., Craig A.J., Hawkins B.C. Encyclopedia of Reagents for Organic Synthesis. 2016. 1–6. https://doi.org/10.1002/047084289X.re063m.pub2
  7. Rao H.M., Holkar A.G., Ayyangar N.R. Tetrahedron Lett. 1990, 31, 3343–3346. https://doi.org/10.1016/S0040-4039(00)89060-7
  8. Li S., Shu H., Wang S., Yang W., Tang F., Li X-X., Fan S., Feng Y-S. Org. Lett. 2022, 24, 5710–5714. https://doi.org/10.1021/acs.orglett.2c02108
  9. Li S., Zhang C., Wang S., Yang W., Fang Х., Fan S., Zhang Q., Li X-X., Feng Y-S. Org. Lett. 2024, 26, 1728–1733. https://doi.org/10.1021/acs.orglett.4c00334
  10. Yang Y., Liu J., Kamounah F.S., Ciancaleoni G., Lee J-W. J. Org. Chem. 2021, 86, 16867–16881. https://doi.org/10.1021/acs.joc.1c02077
  11. Sharpe R.J., Johnson J.S. J. Org. Chem. 2015, 80, 9740–9766. https://doi.org/10.1021/acs.joc.5b01844

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