Solvent-free N-Boc deprotection by ex situ generation of hydrogen chloride gas?
Organic & Biomolecular Chemistry Pub Date: 2021-04-30 DOI: 10.1039/D1OB00728A
Abstract
An efficient, scalable and sustainable method for the quantitative deprotection of the tert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate the ex situ generation of hydrogen chloride gas from sodium chloride and sulfuric acid in a two-chamber reactor, introducing a straightforward method for controlled and stoichiometric release of HCl gas. The solvent-free conditions allow deprotection of a wide variety of N-Boc derivatives to obtain the hydrochloride salts in quantitative yields. The procedure obviates the need for any work-up or purification steps providing an uncomplicated green alternative to standard methods. Due to the solvent-free, anhydrous conditions, this method shows high tolerance towards acid sensitive functional groups and furnishes expanded functional group orthogonality.
Recommended Literature
- [1] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [2] An apparatus for testing water by measurement of its electrical conductivity Analyst, 1912,37, 538-543 10.1039/AN9123700538
- [3] An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins? Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois MatheyDalton Trans., 2019,48, 5523-5526 10.1039/C9DT00838A
- [4] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [5] Alternative synthesis of the anti-baldness compound RU58841? RSC Adv., 2014,4, 14143-14148 10.1039/C4RA00332B
- [6] An investigation of surface properties, local elastic modulus and interaction with simulated pulmonary surfactant of surface modified inhalable voriconazole dry powders using atomic force microscopy Michael Kappl,Paul M. Young,Daniela Traini,Sanyog JainRSC Adv., 2016,6, 25789-25798 10.1039/C6RA01154C
- [7] An anti-leakage liquid metal thermal interface material Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng ChuRSC Adv., 2020,10, 18824-18829 10.1039/D0RA02351E
- [8] An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system? Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai ZhangRSC Adv., 2014,4, 49995-50002 10.1039/C4RA08740B
- [9] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [10] Acenaphthenic hopanoids, a novel series of aromatised Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre AlbrechtChem. Commun., 2001, 1976-1977 10.1039/B105198A
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)