Rapid deracemization through solvent cycling: proof-of-concept using a racemizable conglomerate clopidogrel precursor

Sjoerd W. van Dongen; Iaroslav Baglai; Michel Leeman; Richard M. Kellogg; Bernard Kaptein; Willem L. Noorduin

doi:10.1039/D3CC00332A

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Rapid deracemization through solvent cycling: proof-of-concept using a racemizable conglomerate clopidogrel precursor†

Sjoerd W. van Dongen,

^a Iaroslav Baglai,

^a Michel Leeman,

^b Richard M. Kellogg,^b Bernard Kaptein

*^c and Willem L. Noorduin

*^ad

Author affiliations

* Corresponding authors

^a AMOLF, Science Park 104, Amsterdam 1098 XG, The Netherlands
E-mail: bernard.kaptein@innosyn.com, noorduin@amolf.nl

^b Symeres, Kadijk 3, Groningen 9747 AT, The Netherlands

^c InnoSyn BV, Urmonderbaan 22, Geleen 6167 RD, The Netherlands

^d Van’t Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, Amsterdam, The Netherlands

Abstract

We demonstrate that a conglomerate-forming clopidogrel precursor undergoing solution phase racemization can be deracemized through cyclic solvent removal and re-addition. We establish that the combination of slow growth and fast dissolution of crystals is ideal for rapid deracemization, which we achieve by repurposing a Soxhlet apparatus to realize the slow removal and fast re-addition of solvent autonomously.

This article is part of the themed collection: Chemical Communications HOT Articles 2023

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Article information

DOI: https://doi.org/10.1039/D3CC00332A
Article type: Communication
Submitted: 23 Jan 2023
Accepted: 17 Feb 2023
First published: 20 Feb 2023
This article is Open Access

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Chem. Commun., 2023,59, 3838-3841

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Rapid deracemization through solvent cycling: proof-of-concept using a racemizable conglomerate clopidogrel precursor

S. W. van Dongen, I. Baglai, M. Leeman, R. M. Kellogg, B. Kaptein and W. L. Noorduin, Chem. Commun., 2023, 59, 3838 DOI: 10.1039/D3CC00332A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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Chemical Communications

Rapid deracemization through solvent cycling: proof-of-concept using a racemizable conglomerate clopidogrel precursor†

Abstract

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Rapid deracemization through solvent cycling: proof-of-concept using a racemizable conglomerate clopidogrel precursor

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