102089-74-7Relevant articles and documents
Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for Boc protection of amines
Akbari, Jafar,Heydari, Akbar,Ma'mani, Leila,Hassan Hosseini, Seyed
, p. 544 - 547 (2010)
An efficient and practical protocol for the chemoselective N-Boc protection of various structurally different aryl, aliphatic and heterocyclic amines was carried out with (Boc)2O using protic 1, 1, 3, 3-tetra-methylguanidinium acetate (10 mol%) as recyclable catalyst under solvent free condition at ambient temperature. No competitive side reactions (isocyanate, urea and N, N-di-Boc) were observed. α-Amino alcohols afforded the N-Boc-derivative without oxazolidinone formation.
Visible-Light-Induced Intermolecular Oxyimination of Alkenes
Li, Jun,Yuan, Yong,Bao, Xiazhen,Sang, Tongzhi,Yang, Jie,Huo, Congde
, p. 3712 - 3717 (2021)
An intermolecular vicinal O-N difunctionalization reaction of olefins with oxime esters through energy transfer catalysis has been developed.
Chiral N-Protected β-Iodoamines from α-Aminoacids: a General Synthesis
Caputo, Romualdo,Cassano, Ersilia,Longobardo, Luigi,Palumbo, Giovanni
, p. 167 - 168 (1995)
N-Protected D- or L-β-iodoamines (as 2), which are useful intermediates for the preparation of chiral β-aminoacids, are obtained smoothly from β-aminols (as 1) in two steps and high yields.
Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity
Agami, Claude,Couty, Francois,Hamon, Louis,Venier, Olivier
, p. 4509 - 4512 (1993)
Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AMI calculations.
Magnetic nanoparticles catalyzed N-tert-butoxycarbonylation of Amines and amine derivatives
Akbari, Jafar,Sajirani, Soghra B.,Nezhad, Jafar M.,Heydari, Akbar
, p. 165 - 168 (2012)
A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using magnetically recoverable γ-Fe2O3@SiO 2 nanoparticles is reported. The catalyst can be easily recovered and recycled without a significant loss in the catalytic activity. No competitive side reactions, such as formation of isocyanate, urea, oxazolidinone, and N,N-di-Boc derivatives were obsereved.
A new scaffold for amide ligation
Marinzi, Chiara,Bark, Steven J.,Offer, John,Dawson, Philip E.
, p. 2323 - 2328 (2001)
Highly chemoselective amide forming ligation reactions have facilitated the synthetic access to proteins and other amide-linked bioconjugates. In order to generalize this approach, a Nα-2-phenyl ethanethiol scaffold has been developed to promote S to N acyl transfer in a manner analogous to native chemical ligation with N-terminal cysteine residues. Analysis of scaffold-mediated ligation reactions in aqueous solution indicate that the ligation rate at Xaa-Gly junctions is sufficient for the synthesis of large polypeptides. In addition, it was found that the ligation rate is independent of the stereo center in the scaffold and S-to N-acyl transfer is rate limiting. These studies indicate that the Nα -2-phenyl ethanethiol scaffold is a good candidate for the development of a ligation chemistry for the formation of Xaa-Gly peptides and other unhindered amides. Copyright
Microwave thermolysis IV: Selective deprotection of MPM ethers using clay supported ammonium nitrate 'clayan' in dry media
Yadav,Meshram,Sudershan Reddy,Sumithra
, p. 3043 - 3046 (1998)
Selective deprotection of (4-methoxyphenyl)-methyl (MPM) ethers using clay supported ammonium nitrate under microwave irradiation is described. The use of expensive reagents and problems associated with slurry reactions are avoided.
A mild and selective cleavage of p-methoxybenzyl Ethers by CBr4-MeOH
Yadav,Reddy, B. V. Subba
, p. 566 - 567 (2000)
p-Methoxybenzyl ethers were selectively deprotected to the corresponding alcohols and phenols in high yields by CBr4 in refluxing methanol under neutral reaction conditions.
1,1,1,3,3,3-Hexafluoroisopropanol: A recyclable organocatalyst for N-Boc protection of amines
Heydari, Akbar,Khaksar, Samad,Tajbakhsh, Mahmood
, p. 3126 - 3130 (2008)
A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as solvent and catalyst is described. The catalyst can be readily separated from the reaction products and recovered for direct reuse. No competitive side reactions such as formation of isocyanate, urea, and N,N-di-Boc were observed. α-Amino alcohols afforded the N-Boc derivatives without oxazolidinone formation. Georg Thieme Verlag Stuttgart.
Platinum nanoparticles supported on zirconia mediated synthesis of N-acyl and N-(tert-butoxycarbonyl)amines from nitroarenes and azides
Kantam, M. Lakshmi,Reddy, R. Sudarshan,Srinivas,Chakravarti,Sreedhar,Figueras,Venkat Reddy, Ch.
, p. 96 - 101 (2012)
A convenient and useful protocol has been designed for the synthesis of N-aryl acetamides from the corresponding nitro compounds via a reductive N-acylation process using bi-functional, recyclable heterogeneous platinum nanoparticles supported on zirconia [Pt(0)/ZrO2] catalyst, employing molecular hydrogen as the environmentally benign reductant and the corresponding anhydrides as acylating agents. N-Boc protected amines were also synthesized in similar lines, from the corresponding azides. The reaction is successfully performed under mild conditions to afford good to excellent yields of the products. The solid bifunctional-catalyst, Pt(0)/ZrO2 is quantitatively recovered by simple centrifugation and reused for multiple cycles with consistent activity and selectivity.
