Efficient and Practical Deacylation Reaction System in a Continuous Packed-Bed Reactor

The ester deacylation reaction is widely applied in organic synthesis for preparing desired hydroxy compounds, as the acyl group is often used for protecting the hydroxyl group. This reaction is usually performed by acid, base, or enzyme catalysts, which have to be removed by complicated workups suc...

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Veröffentlicht in:Organic process research & development 2019-04, Vol.23 (4), p.654-659
Hauptverfasser: Yasukouchi, Hiroaki, Machida, Koji, Nishiyama, Akira, Mitsuda, Masaru
Format: Artikel
Sprache:eng
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Zusammenfassung:The ester deacylation reaction is widely applied in organic synthesis for preparing desired hydroxy compounds, as the acyl group is often used for protecting the hydroxyl group. This reaction is usually performed by acid, base, or enzyme catalysts, which have to be removed by complicated workups such as extraction or filtration in batch mode. Therefore, a simple deacylation process is desirable to improve productivity, especially at the industrial scale. In this work, we established an efficient and practical packed-bed reactor system for undertaking the deacylation reaction using an anion-exchange resin that provides a simple process compared with batch processing. We also demonstrated that this technique is applicable to the preparation of a wide variety of desired pharmaceutical intermediates containing hydroxy groups in good to excellent yields.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.8b00393