European Journal of Chemistry 2012, 3(3), 305-309 | doi: https://doi.org/10.5155/eurjchem.3.3.305-309.610 | Get rights and content






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Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst


Roubila Belghiche (1) , Zinelaabidine Cheraiet (2,*) , Malika Berredjem (3) , Mostefa Abbessi (4) , Nour-Eddine Aouf (5)

(1) Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria
(2) Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria
(3) Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria
(4) Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria
(5) Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria
(*) Corresponding Author

Received: 07 Apr 2012 | Accepted: 19 May 2012 | Published: 30 Sep 2012 | Issue Date: September 2012

Abstract


A series of sulfamides containing two protecting groups have been synthesized starting from N-benzoylaminoacids derivatives of (glycine, alanine, valine, leucine, phenylalanine), chlorosulfonylisocyanate and primary amines. Selective deprotection of the cyclic or linear sulfamides and amines has been achieved by treatment with heteropolyacid, which is easily recoverable and reusable. This method represents a reasonable alternative to the previous reported deprotection procedures.

3_3_305_309_800


Keywords


Catalyst; Cyclosulfamides; Protective group; N-Boc deprotection; Dawson heteropolyacid; Heterogeneous catalysis

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DOI: 10.5155/eurjchem.3.3.305-309.610

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Funding information


Algerian Ministry of Scientific Research (Direction Générale de la Recherche Scientifique et du Développement Technologique, DGRS-DT)

Citations

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[1]. Hacène K’tir, Aïcha Amira, Malika Berredjem, Nour-Eddine Aouf
A New, Efficient, and Catalyst-free Microwave-assisted Approach for Formation of O-tert-Butoxy Carbonates
Chemistry Letters  43(6), 851, 2014
DOI: 10.1246/cl.140075
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[2]. Aïcha Amira, Hacène K’tir, Malika Berredjem, Nour-Eddine Aouf
A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions
Monatshefte für Chemie - Chemical Monthly  145(3), 509, 2014
DOI: 10.1007/s00706-013-1094-4
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[3]. Juan M. López-Soria, Sixto J. Pérez, J. Nicolás Hernández, Miguel A. Ramírez, Víctor S. Martín, Juan I. Padrón
A practical, catalytic and selective deprotection of a Boc group in N,N′-diprotected amines using iron(iii)-catalysis
RSC Advances  5(9), 6647, 2015
DOI: 10.1039/C4RA12143K
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[4]. Salah Lakrout, Hacène K'tir, Aïcha Amira, Malika Berredjem, Nour-Eddine Aouf
A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions
RSC Adv.  4(31), 16027, 2014
DOI: 10.1039/C4RA01346H
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[5]. Abderrehmane Djemili, Salah Lakrout, Zinelaabidine Cheraiet, Malika Berredjem, Nour-Eddine Aouf
A simple and highly efficient solvent- and catalyst-free synthesis of novelN-sulfamoyl imines
Green Chemistry Letters and Reviews  8(1), 48, 2015
DOI: 10.1080/17518253.2015.1027287
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[6]. Swapan Majumdar, Jhinuk De, Ankita Chakraborty, Dipanwita Roy, Dilip K. Maiti
A protic ionic liquid catalyzed strategy for selective hydrolytic cleavage of tert-butyloxycarbonyl amine (N-Boc)
RSC Advances  5(5), 3200, 2015
DOI: 10.1039/C4RA13419B
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How to cite


Belghiche, R.; Cheraiet, Z.; Berredjem, M.; Abbessi, M.; Aouf, N. Eur. J. Chem. 2012, 3(3), 305-309. doi:10.5155/eurjchem.3.3.305-309.610
Belghiche, R.; Cheraiet, Z.; Berredjem, M.; Abbessi, M.; Aouf, N. Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst. Eur. J. Chem. 2012, 3(3), 305-309. doi:10.5155/eurjchem.3.3.305-309.610
Belghiche, R., Cheraiet, Z., Berredjem, M., Abbessi, M., & Aouf, N. (2012). Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst. European Journal of Chemistry, 3(3), 305-309. doi:10.5155/eurjchem.3.3.305-309.610
Belghiche, Roubila, Zinelaabidine Cheraiet, Malika Berredjem, Mostefa Abbessi, & Nour-Eddine Aouf. "Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst." European Journal of Chemistry [Online], 3.3 (2012): 305-309. Web. 31 May. 2020
Belghiche, Roubila, Cheraiet, Zinelaabidine, Berredjem, Malika, Abbessi, Mostefa, AND Aouf, Nour-Eddine. "Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst" European Journal of Chemistry [Online], Volume 3 Number 3 (30 September 2012)

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DOI Link: https://doi.org/10.5155/eurjchem.3.3.305-309.610

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