Convenient Preparation of tert-Butyl Amino Acid Esters from tert-Butanol-Reference-Cited by-同舟云学术

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

Published:2023-05-01 Issue:3 Volume:49 Page:291-295
ISSN:1998-2860
Container-title:Биоорганическая химия
language:
Short-container-title:RUBI

Author:

Azev V. N.¹,Chulin A. N.¹,Molchanov M. V.²,Miroshnikov A. I.³

Affiliation:

1. Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS,

2. Istitute for Theoretical and Experimental Biophysics RAS

3. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

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.

Publisher

The Russian Academy of Sciences

Reference20 articles.

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