Convenient Preparation of tert-Butyl Amino Acid Esters from tert-Butanol

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A preparation of tert-butyl esters of amino acid is described that proceeds from protected amino acids and tert-butanol using anhydrous magnesium sulfate and an excess of boron trifluoride diethyl etherate as additional reagents. The method affords tert-butyl esters in good yields and a variety of amino acid side chains and substituents tolerate the reaction conditions.

About the authors

V. N. Azev

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS,

Author for correspondence.
Email: viatcheslav.azev@bibch.ru
Russia, 142290, Puschino, prosp. Nauki 6

A. N. Chulin

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS,

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Puschino, prosp. Nauki 6

M. V. Molchanov

Istitute for Theoretical and Experimental Biophysics RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Puschino, Institutskaya ul. 3

A. I. Miroshnikov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: viatcheslav.azev@bibch.ru
Russia, 117997, Moscow, ul. Miklukho-Maklaya 16/10

References

  1. Isidro-Llobet A., Álvarez M., Albericio F. // Chem. Rev. 2009. V. 109. P. 2455–2504. https://doi.org/10.1021/cr800323s
  2. Kohlbau H.-J., Thürmer R., Voelter W. // Synthesis of Peptides and Peptidomimetics (Houben-Weyl E22a: Methods of Organic Chemistry) / Eds. Goodman M., Felix A.M., Moroder L., Toniolo C. Stuttgart and New York: Georg Thieme Verlag, 2002. P. 193–237.
  3. Thürmer R., Kohlbau H.-J., Voelter W. // Synthesis of Peptides and Peptidomimetics (Houben-Weyl E22a: Methods of Organic Chemistry) / Eds. Goodman M., Felix A.M., Moroder L., Toniolo C. Stuttgart and New York: Georg Thieme Verlag, 2002. P. 238–259.
  4. Wuts P.G.M. // Greene’s Protective Groups in Organic Synthesis. Hoboken, New Jersey: John Wiley & Sons, Inc., 2014. P. 686–836.
  5. Taschner E., Liberek B., Wasielewski Cz., Biernat J. // Angew. Chem. 1959. V. 71. P. 743–743. https://doi.org/10.1002/ange.19590712307
  6. Roeske R.W. // Chem. & Ind. 1959. V. 23. P. 1121–1122.
  7. Roeske R. // J. Org. Chem. 1963. V. 28. P. 1251–1253. https://doi.org/10.1021/jo01040a022
  8. Anderson G.W., Callahan F.M. // J. Am. Chem. Soc. 1960. V. 82. P. 3359–3363. https://doi.org/10.1021/ja01498a032
  9. Wright S.W., Hageman D.L., Wright A.S., McClure L.D. // Tetrahedron Lett. 1997. V. 38. P. 7345–7348. https://doi.org/10.1016/S0040-4039(97)01792-9
  10. Berridge M.S., Burnazi E.M. // J. Labelled Cpd. Radiopharm. 2001. V. 44. P. 859–864. https://doi.org/10.1002/jlcr.510
  11. McDermott T.S., Bhagavatula L., Borchardt T.B., Engstrom K.M., Gandarilla J., Kotecki B.J., Kruger A.W., Rozema M.J., Sheikh A.Y., Wagaw S.H., Wittenberger S.J. // Org. Proc. Res. Dev. 2009. V. 13. P. 1145–1155. https://doi.org/10.1021/op900197r
  12. Chaleix V., Sol V., Huang Y.-M., Guilloton M., Granet R., Blais J.C., Krausz P. // Eur. J. Org. Chem. 2003. V. 2003. P. 1486–1493. https://doi.org/10.1002/ejoc.200390208
  13. Schnabel E., Schüssler H. // Liebigs Ann. Chem. 1965. V. 686. P. 229–238. https://doi.org/10.1002/jlac.19656860127
  14. Kadaba P.K., Carr M., Tribo M., Triplett J., Glasser A.C. // J. Pharm. Sci. 1969. V. 58. P. 1422–1423. https://doi.org/10.1002/jps.2600581131
  15. Sowa F.J., Nieuwland J.A. // J. Am. Chem. Soc. 1936. V. 58. P. 271–272. https://doi.org/10.1021/ja01293a022
  16. Posner G.H., Shulman-Roskes E.M., Oh Ch. Ho, Carry J.-Ch., Green J.V., Clark A.B., Dai H., Anjeh T.E.N. // Tetrahedron Lett. 1991. V. 32. P. 6489–6492. https://doi.org/10.1016/0040-4039(91)80200-P
  17. Topchiev A.V., Zavgorodnii S.V., Paushkin Ya.M. // Boron Fluoride and Its Compounds as Catalysts in Organic Chemistry / Eds. Doering W., Barton D.H.R. Pergamon, 1958. P. 205–226. https://doi.org/10.1016/B978-0-08-009128-0.50011-2
  18. Armarego W.L.F., Chai C. // Purification of Laboratory Chemicals, 6th ed. Oxford: Butterworth-Heinemann, 2012.
  19. Hueber A., Gimbert Y., Langevin G., Galano J.-M., Guy A., Durand T., Cenac N., Bertrand-Michel J., Tabet J.-C. // Amino Acids. 2022. V. 54. P. 241–250. https://doi.org/10.1007/s00726-021-03109-1
  20. Benassi R., Folli U., Schenetti L., Taddei F. // Adv. Het. Chem. 1987. V. 41. P. 75–186. https://doi.org/10.1016/S0065-2725(08)60161-0

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 В.Н. Азев, А.Н. Чулин, М.В. Молчанов, А.И. Мирошников