Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Lipase- and Base Catalyzed Synthesis of Enantiopure β-Blocker (S)-Atenolol

Version 1 : Received: 19 February 2024 / Approved: 19 February 2024 / Online: 19 February 2024 (12:19:27 CET)

A peer-reviewed article of this Preprint also exists.

Hansen, M.B.; Tennfjord, A.L.; Blindheim, F.H.; Bocquin, L.H.Y.; Jacobsen, E.E. Synthesis of Enantiopure (S)-Atenolol by Utilization of Lipase-Catalyzed Kinetic Resolution of a Key Intermediate. Int. J. Mol. Sci. 2024, 25, 3497. Hansen, M.B.; Tennfjord, A.L.; Blindheim, F.H.; Bocquin, L.H.Y.; Jacobsen, E.E. Synthesis of Enantiopure (S)-Atenolol by Utilization of Lipase-Catalyzed Kinetic Resolution of a Key Intermediate. Int. J. Mol. Sci. 2024, 25, 3497.

Abstract

(S)-Atenolol ((S)-2-(4-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide) has been synthesized in >99% ee with use of Candida antarctica lipase B from Syncozymes (Shanghai, China), in a kinetic resolution of the corresponding racemic chlorohydrin. Deprotonation of the starting phenol building block was base catalyzed. The enantiopurity of the chlorohydrin building block remained unchanged upon subsequent amination. All four steps in the synthesis protocol have been optimized compared to previously reported methods, which makes this new protocol more sustainable and in accordance with green chemistry principles compared to previously reported protocols.

Keywords

Enantiopure (S)-atenolol, Candida antarctica lipase B, base catalysis, Chiralcel OD-H column

Subject

Chemistry and Materials Science, Organic Chemistry

Comments (0)

We encourage comments and feedback from a broad range of readers. See criteria for comments and our Diversity statement.

Leave a public comment
Send a private comment to the author(s)
* All users must log in before leaving a comment
Views 0
Downloads 0
Comments 0


×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.
We use cookies on our website to ensure you get the best experience.
Read more about our cookies here.