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Deprotection of N-Boc Groups under Continuous-Flow High-Temperature Conditions

机译:在连续流动高温条件下对N-BOC基团的脱保护

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摘要

The scope of thermolytic, N-Boc deprotection was studied on 26 compounds from the Pfizer compound library, representing a diverse set of structural moieties. Among these compounds, 12 substrates resulted in clean (>= 95% product) deprotection, and an additional three compounds gave >= 90% product. The thermal de-Boc conditions were found to be compatible with a large number of functional groups. A combination of computational modeling, statistical analysis, and kinetic model fitting was used to support an initial, slow, and concerted proton transfer with release of isobutylene, followed by a rapid decarboxylation. A strong correlation was found to exist between the electrophilicity of the N-Boc carbonyl group and the reaction rate.
机译:在辉瑞化合物库中的26种化合物中研究了热分解,N-Boc脱保护的范围,代表了各种结构部分。 在这些化合物中,导致12种底物干净(> = 95%产物)脱保护,另外三种化合物得到> = 90%产物。 发现热除滑条件与大量官能团相容。 使用计算建模,统计分析和动力学模型配件的组合用于支持初始,慢,并与异丁烯释放的初始,缓慢的质子转移,然后是快速脱羧。 发现了N-Boc羰基的亲电和反应速率之间存在强烈的相关性。

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  • 来源
    《The Journal of Organic Chemistry》 |2019年第8期|共10页
  • 作者单位

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

    Pfizer Inc Med Sci Worldwide Res &

    Dev Eastern Point Rd Groton CT 06340 USA;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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