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A novel use of catalytic zinc-hydroxyapatite columns for the selective deprotection of N-tert-butyloxycarbonyl (BOC) protecting group using flow chemistry

A novel use of catalytic zinc-hydroxyapatite columns for the selective deprotection of... The development of a single step flow process for the deprotection of the common protecting group tert-butyloxycarbonyl (BOC) is presented. Conventional BOC deprotection methods can require up to 24 h to fully deprotect compounds and may require cleanup due to undesired side products [1]. Long reaction times, high temperature, and undesired destruction of other protecting groups or the compound itself, have been reported in alternative methods presented recently in the literature [2]. The process presented herein allows for near quantitative and selective deprotection of the BOC protecting group in 30 min at 150 °C in flow using a zinc-hydroxyapatite (Zn-HAP) column. A selection of nineteen examples with diverse functionalities were used to demonstrate the application of this catalyst in flow. The products of the reactions were analyzed by HPLC, LC-MS and CE to determine the yield and purity. In comparison to the standard deprotection methods our process yields a clean, fast and selective method to deprotect N-Boc products and yields the desired corresponding free amine products. Of the nineteen compounds, nine transformations resulted in clean products (≥90 % ). One of these products was tested for racemization and the product remained enantiopure. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

A novel use of catalytic zinc-hydroxyapatite columns for the selective deprotection of N-tert-butyloxycarbonyl (BOC) protecting group using flow chemistry

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2020
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-019-00052-x
Publisher site
See Article on Publisher Site

Abstract

The development of a single step flow process for the deprotection of the common protecting group tert-butyloxycarbonyl (BOC) is presented. Conventional BOC deprotection methods can require up to 24 h to fully deprotect compounds and may require cleanup due to undesired side products [1]. Long reaction times, high temperature, and undesired destruction of other protecting groups or the compound itself, have been reported in alternative methods presented recently in the literature [2]. The process presented herein allows for near quantitative and selective deprotection of the BOC protecting group in 30 min at 150 °C in flow using a zinc-hydroxyapatite (Zn-HAP) column. A selection of nineteen examples with diverse functionalities were used to demonstrate the application of this catalyst in flow. The products of the reactions were analyzed by HPLC, LC-MS and CE to determine the yield and purity. In comparison to the standard deprotection methods our process yields a clean, fast and selective method to deprotect N-Boc products and yields the desired corresponding free amine products. Of the nineteen compounds, nine transformations resulted in clean products (≥90 % ). One of these products was tested for racemization and the product remained enantiopure.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jun 11, 2020

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