Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

Nathaniel George; Samuel Ofori; Sean Parkin; Samuel G. Awuah

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Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

机译：使用草酰氯温和的脱乙酰脱落（N-BOC）基团的脱保护

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We report a mild method for the selective deprotection of the N -Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1–4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.

机译：我们报告了一种温和的方法，用于通过在甲醇中使用草酰氯，包括在结构上不同的化合物中选择性脱保护N-BOC基团，包括脂族，芳族和杂环基材。反应在室温条件下进行1-4小时，产率高达90％。将这种温和的方法应用于杂交药物活性化合物Fc1，其是IDO1和DNAPOLγ的新型双重抑制剂。假设涉及草酰氯的亲电特征的更广泛的机制用于这种脱保护策略。

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《RSC Advances》 |2020年第40期|共10页
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Nathaniel George; Samuel Ofori; Sean Parkin; Samuel G. Awuah;
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1. Mild deprotection of theN-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride [J] . George Nathaniel, Ofori Samuel, Parkin Sean, RSC Advances . 2020,第40期

机译：使用草酰氯温和的脱乙酰氧基羰基（N-BOC）基团
2. Microwave-assisted N-Boc deprotection under mild basic conditions using K3PO4·H2O in MeOH [J] . Srinivasa Reddy Dandepally, Alfred L Williams Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第9期

机译：在温和的碱性条件下，使用MeOH中的K3PO4·H2O进行微波辅助的N-Boc脱保护
3. A mild and selective method for the N-Boc deprotection by sodium carbonate [J] . El Kazzouli S, Koubachi J, Berteina-Raboin S, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2006,第48期

机译：温和选择性的碳酸钠脱除N-Boc的方法
4. The Photochemical Degradation of Chloral and Oxalyl Chloride [C] . Lorraine Nolan, Tanya Kelly, John Wenger, NATO Advanced Research Workshop on Global Atmospheric Change and its Impact on Regional Air Quality . 2002

机译：氯和草氯的光化学劣化
5. I. Tertiary aryl sulfonamides as new cross coupling partners for nickel catalyzed Kumada-Corriu-Tamao reductive and carbon-carbon bond forming cross coupling reactions. II. N-sulfonyl deprotection under mild nickel(0) catalyzed Kumada-Corriu-Tamao coupling conditions and development of the N-Ans protecting group. III. Synthesis and application of 3,3'-di-(2-pyridyl)-1,1'-bi-2-naphthol ligands [D] . Milburn, Robert Ronald 2004

机译：I.叔芳基磺酰胺作为镍催化的Kumada-Corriu-Tamao还原和碳-碳键形成交叉偶联反应的新交叉偶联伴侣。二。在温和的镍（0）下N-磺酰基脱保护催化了Kumada-Corriu-Tamao偶联条件和N-Ans保护基的发展。三， 3,3'-二-（2-吡啶基）-1,1'-bi-2-萘酚配体的合成及应用
6. A novel and highly efficient esterification process using triphenylphosphine oxide with oxalyl chloride [O] . Mingzhu Jia, Lixue Jiang, Fanfan Niu, 2018

机译：三苯基氧化膦与草酰氯的新型高效酯化工艺
7. A Simple and Efficient Green Method for the Deprotection of N-Boc in Various Structurally Diverse Amines under Water-mediated Catalyst-free Conditions [O] . Aouf Nour-Eddine, Berredjem Malika, Jamel Zoubir, 2012

机译：一种简单高效的绿色方法，在无水介导的条件下，将各种结构多样的胺中的N-Boc脱保护

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

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