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Deprotection of N-Boc Groups under Continuous-Flow High-Temperature Conditions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-01-08 00:00:00 , DOI: 10.1021/acs.joc.8b02909 Bryan Li 1 , Ruizhi Li 1 , Peter Dorff 1 , J. Christopher McWilliams 1 , Robert M. Guinn 1 , Steven M. Guinness 1 , Lu Han 1 , Ke Wang 1 , Shu Yu 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-01-08 00:00:00 , DOI: 10.1021/acs.joc.8b02909 Bryan Li 1 , Ruizhi Li 1 , Peter Dorff 1 , J. Christopher McWilliams 1 , Robert M. Guinn 1 , Steven M. Guinness 1 , Lu Han 1 , Ke Wang 1 , Shu Yu 1
Affiliation
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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.
中文翻译：
连续流高温条件下N -Boc基团的脱保护
对辉瑞化合物库中的26种化合物进行了热解N- Boc脱保护的研究，这些化合物代表了不同的结构部分。在这些化合物中，有12种底物导致干净的（≥95％的产品）脱保护，另外三种化合物给出了≥90％的产品。发现热de-Boc条件与大量官能团相容。计算模型，统计分析和动力学模型拟合的组合用于支持初始，缓慢和一致的质子转移，并释放异丁烯，然后快速脱羧。发现N- Boc羰基的亲电性与反应速率之间存在强相关性。
更新日期：2019-01-08
中文翻译：
连续流高温条件下N -Boc基团的脱保护
对辉瑞化合物库中的26种化合物进行了热解N- Boc脱保护的研究，这些化合物代表了不同的结构部分。在这些化合物中，有12种底物导致干净的（≥95％的产品）脱保护，另外三种化合物给出了≥90％的产品。发现热de-Boc条件与大量官能团相容。计算模型，统计分析和动力学模型拟合的组合用于支持初始，缓慢和一致的质子转移，并释放异丁烯，然后快速脱羧。发现N- Boc羰基的亲电性与反应速率之间存在强相关性。
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