28991-69-7Relevant academic research and scientific papers
A greener, efficient and catalyst-free ultrasonic-assisted protocol for the n-fmoc protection of amines
Mansouri, Rachida,Aouf, Zineb,Lakrout, Salah,Berredjem, Malika,Aouf, Nour-Eddine
, p. 546 - 550 (2016/03/19)
A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.
N-Urethane protection of amines and amino acids in an ionic liquid
Di Gioia,Gagliardi,Leggio,Leotta,Romio,Liguori
, p. 63407 - 63420 (2015/08/11)
An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.
A synthetic approach to N -aryl carbamates via copper-catalyzed Chan-Lam coupling at room temperature
Moon, Soo-Yeon,Kim, U. Bin,Sung, Dan-Bi,Kim, Won-Suk
, p. 1856 - 1865 (2015/02/19)
A mild and efficient synthesis of N-arylcarbamates was achieved by reacting azidoformates with boronic acids in the presence of 10 mol % of copper chloride catalyst. The reaction proceeds readily in an open flask at room temperature without additional base, ligand, or additive. Rapid access to urea analogues via a two-step one-pot procedure is enabled by reacting N-arylcarbamates with aluminum-amine complexes. In addition, among several boronic acid derivatives prepared, dimethylphenyl boronate was found to react rapidly in its reaction with benzyl azidoformate, invoking in situ generation of this species in the catalytic cycle.
Aqueous MW eco-friendly protocol for amino group protection
Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
, p. 18751 - 18760 (2015/06/15)
In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.
Chemoselective N-deacetylation under mild conditions
Sultane, Prakash R.,Mete, Trimbak B.,Bhat, Ramakrishna G.
, p. 261 - 264 (2014/01/06)
A mild and efficient chemoselective N-deacetylation using the Schwartz reagent at room temperature in rapid time is described. The mild and neutral conditions enable orthogonal N-deacetylation in the presence of some of the common protecting groups (viz. Boc, Fmoc, Cbz, Ts). The deprotection conditions did not induce any epimerization at the chiral amino centre.
CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES
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Page/Page column 5-6; 32, (2011/11/30)
The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.
An efficient and expeditious Fmoc protection of amines and amino acids in aqueous media
Gawande, Manoj B.,Branco, Paula S.
supporting information; experimental part, p. 3355 - 3359 (2012/01/06)
A new and environmentally friendly Fmoc protection of a variety of aliphatic and aromatic amines, amino acids, amino alcohols and amino phenols is reported in aqueous media under mild and catalyst-free conditions. The reaction proved to be chemoselective in presence of ambident nucleophiles.
Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions
Hutchby, Marc,Houlden, Chris E.,Gair Ford,Tyler, Simon N. G.,Gagne, Michel R.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
supporting information; experimental part, p. 8721 - 8724 (2010/01/16)
Bigger is better: Sterically hindered dialkyl ureas undergo nucleophilic substitution at dramatically faster rates than their less hindered counterparts (see scheme). Steric decompression upon the formation of an intermediate isocyanate can explain this c
Convenient method for the preparation of carbamates, carbonates, and thiocarbonates
Shimizu, Mamoru,Sodeoka, Mikiko
, p. 5231 - 5234 (2008/09/17)
(Chemical Equation Presented) A convenient, rapid, and efficient method for the preparation of carbamates from amines with 1-alkoxycarbonyl-3-nitro-1,2,4- triazole transfer reagents is reported. Reactions of newly synthesized stable crystalline reagents with alkyl amines were completed in a few minutes without any additional base, and highly pure carbamates were obtained without chromatographic purification. These highly active reagents are also useful for the selective protection of nucleobases and preparation of carbonates and thiocarbonates.
Solution-Phase Parallel Synthesis of Carbamates Using Polymer-Bound N-Hydroxysuccinimide
Sumiyoshi, Hirokazu,Shimizu, Takafumi,Katoh, Miho,Baba, Yoshiyasu,Sodeoka, Mikiko
, p. 3923 - 3926 (2007/10/03)
(Matrix Presented) A convenient method for the synthesis of carbamates using polymer-supported N-hydroxysuccinimide is described. Various carbamates were synthesized in highly pure form without the need for chromatographic purification. This new "catch an
