European Journal of Chemistry 2012, 3(3), 305-309. doi:10.5155/eurjchem.3.3.305-309.610

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

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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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
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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
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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
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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
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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. 22 Sep. 2019
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)

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

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