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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
Journal of Flow Chemistry ( IF 2.0 ) Pub Date : 2020-02-11 , DOI: 10.1007/s41981-019-00052-x
Evan Langille , Christina S. Bottaro , Alexandre Drouin

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.



中文翻译:

催化锌-羟基磷灰石色谱柱在N-叔丁氧羰基(BOC)保护基的选择性脱保护中的新应用

提出了用于常规保护基叔丁氧羰基(BOC)脱保护的单步流动方法的开发。常规的BOC脱保护方法可能需要长达24小时才能完全脱保护化合物,并且由于不希望有的副产物而可能需要清洗[1]。最近在文献[2]中提出的替代方法中已经报道了较长的反应时间,高温以及对其他保护基或化合物本身的不希望的破坏。本文介绍的方法允许使用锌-羟基磷灰石(Zn-HAP)色谱柱在150°C下于30分钟内对BOC保护基进行近乎定量和选择性的脱保护。选择了十九个具有不同功能的实例,以证明该催化剂在流动中的应用。反应产物通过HPLC分析,LC-MS和CE确定产量和纯度。与标准脱保护方法相比,我们的方法产生了一种清洁,快速和选择性的方法来脱保护N-Boc产物,并产生了所需的相应游离胺产物。在这19种化合物中,有9种转化产生了清洁产品(≥90%)。测试了其中一种产品的消旋性,该产品保持对映纯。

更新日期:2020-02-11
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