cas 60144-52-7, tert-butyl 3-methoxyphenylcarbamate

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Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family
Natural products (NPs) are an important inspirational source for developing drugs and chemical probes. In 1999, the group of ōmura reported the constitutional elucidation of zelkovamycin. Although largely unrecognized so far, this NP displays structural s
Krahn, Daniel,Heilmann, Geronimo,Vogel, Felix C. E.,Papadopoulos, Chrisovalantis,Zweerink, Susanne,Kaschani, Farnusch,Meyer, Hemmo,Roesch, Alexander,Kaiser, Markus
supporting information
p. 8524 - 8531
(2020/07/02)

Organic/inorganic Fe3O4@MCM-41@Zr-piperazine: An impressive magnetite nanocatalyst for N-Tert-Butoxycarbonylation of amines
Fe3O4@MCM-41@Zirconium magnetic nanoparticles modified with piperazine (Fe3O4@MCM-41@Zr-piperazine), as a newly reported catalyst, shows excellent catalytic activity in N-tertbutoxycarbonylation of amines under the mild and solvent-free conditions. Accordingly, different derivatives of N-tert-butylcarbamates owning diverse aliphatic, aromatic and heteroaromatic amines were prepared efficiently. Good performance of this method for the majority of used complex or acidsensitive substrates and facile separation of this nanocatalyst due to its superparamagnetic nature from the reaction mixture via an external magnetic field for several times are the most important striking features of this protocol.
Pourhasan-Kisomi, Reyhaneh,Shirini, Farhad,Golshekan, Mostafa
p. 3859 - 3870
(2019/05/08)

Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.
Lanzi, Matteo,Merad, Jérémy,Boyarskaya, Dina V.,Maestri, Giovanni,Allain, Clémence,Masson, Géraldine
supporting information
p. 5247 - 5250
(2018/09/13)

Hypoxia-Activated Anticancer Prodrug for Bioimaging, Tracking Drug Release, and Anticancer Application
A novel anticancer theranostic prodrug, FDU-DB-NO2, specifically activated by hypoxia for selective two-photon imaging hypoxia status, real-time tracking drug release, and solid tumor therapy was designed. The devised prodrug consists of an anticancer drug floxuridine (FDU), a fluorescence dye precursor 4′-(diethylamino)-1,1′-biphenyl-2-carboxylate (DB), and a hypoxic trigger 4-nitrobenzyl group. In normal cells, FDU-DB-NO2 is "locked". Whereas in tumor cells, the prodrug is "unlocked" by hypoxia and results in fluorescent dye 7-(diethylamino)coumarin (CM) generation along with FDU release. The amounts and rates of CM formation and FDU release were controlled by hypoxic status and increased with the decreasing of the O2 concentration. The hypoxic status, distribution of oxygen, and amount of FDU release in tumor cells, spheroids, and tumor tissue could be visualized by fluorescence. FDU-DB-NO2 showed high cytotoxicity against hypoxic MCF-7 and MCG-803 cell lines and no cytotoxicity against normoxic BRL-3A cells and exhibited effective inhibition on tumor growth of MCF-7-cell-inoculated xenograft nude mice. This strategy may provide a promising platform for selective two-photon imaging hypoxia status, real-time tracking drug release, and personalized solid tumor treatment.
Liu, Wei,Liu, Haitong,Peng, Xiaoran,Zhou, Guoqiang,Liu, Dandan,Li, Shenghui,Zhang, Jinchao,Wang, Shuxiang
p. 3332 - 3343
(2018/09/25)

Preparation, characterization and application of 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl) as an efficient dicationic ionic catalyst for the N-Boc protection of amines
In this work, 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl), as a novel Br?nsted acidic ionic catalyst is synthesized and characterized using a series of techniques including FT-IR, TGA, DTA, SEM, pH analysis and Hammett acidity function. This substance can significantly catalyze the N-Boc protection of amines without solvent interference at room temperature. The advantages of this manner are chemoselectivity, short reaction times, suitable yields, excellent yields of the products, without solvent interference and ease of preparation as well as reusability of the catalyst.
Koodehi, Tahereh Ghauri,Shirini, Farhad,Goli-Jolodar, Omid
p. 443 - 456
(2017/01/10)

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles
Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.
Wang, Peng,Farmer, Marcus E.,Huo, Xing,Jain, Pankaj,Shen, Peng-Xiang,Ishoey, Mette,Bradner, James E.,Wisniewski, Steven R.,Eastgate, Martin D.,Yu, Jin-Quan
supporting information
p. 9269 - 9276
(2016/08/05)

Preparation, characterization and application of succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the N-Boc protection of amines
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), as a novel Bronsted acidic ionic liquid is prepared and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass and SEM. This reagent can be used as an efficient catalyst for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, this ionic liquid can be recovered and reused for several times. This journal is
Shirini, Farhad,Jolodar, Omid Goli,Seddighi, Mohadeseh,Borujeni, Hojatollah Takbiri
p. 19790 - 19798
(2015/03/18)

Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
A mild, efficient and eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively short reaction times, excellent yields and low cost, availability and reusability of the catalyst are the striking features of this methodology, which can be considered to be one of the best and general methods for the protection of alcohols, phenols, thiols and amines. In addition, the use of a green reagent in the above-mentioned reactions results in a reduction of environmental pollution and of the cost of the applied methods.
Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali,Aliakbar, Ali-Reza
p. 164 - 170
(2014/03/21)

Palladium-catalyzed γ-selective arylation of zincated Boc-allylamines
The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the products could be directly transformed into valuable γ-arylamines and β-aryl aldehydes.
Millet, Anthony,Baudoin, Olivier
supporting information
p. 3998 - 4000
(2014/08/18)

Iron(III)triflate as a highly efficient, recyclable and green catalyst for the N-Boc protection of amines
Iron (III) triflate was used as an efficient catalyst for N-t-butoxycarbonylation of amines with di-t-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. Only two of the 23 monocarbamates were new. No competitive side reactions such as isocyanate, urea, nor N,N-di-Boc formation were observed. The reported method is mild and has the advantages of low cost, chemoselectivity and, because no solvent is used and the catalyst can be recycled, it is classifiable as a green procedure.
Feng, Chengliang,Chu, Ningning,Zhang, Shuguang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
p. 757 - 760
(2014/01/23)

1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines
1,3-Disulfonic acid imidazolium hydrogen sulfate is easily prepared and used as an efficient and recyclable ionic liquid for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered for several times without loss of activity.
Shirini, Farhad,Khaligh, Nader Ghaffari
p. 386 - 393
(2013/03/14)

Nanocrystalline titania-based sulfonic acid (TiO2-Pr-SO 3H) as a new, highly efficient and recyclable solid acid catalyst for the N-Boc protection of amines at room temperature
Sulfonic acid-functionalized nanoporous titania (TiO2-Pr-SO 3H) was prepared from the reaction of (3-mercaptopropyl) trimethoxysilane and TiO2, then by oxidation of thiols group with hydrogen peroxide. The morphology and acidity of synthesized catalyst was characterized by FT-IR, SEM, TEM, TGA and XRD techniques and Hammett acidity test. The catalytic performance of TiO2-Pr-SO3H was investigated in the N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature. Our novel method is mild, chemoselective and has the advantages such as heterogeneous catalysis, low cost and the recyclability of the catalyst.
Atghia,Sarvi Beigbaghlou
p. 42 - 49
(2013/10/01)

Palladium-catalyzed amidation of aryl halides using 2-dialkylphosphino- 2′-alkoxyl-1,1′-binaphthyl as ligands
Palladium-catalyzed intermolecular C-N bond-forming reactions between aryl halides and amides are described using 2-dialkylphosphino-2′-alkoxyl-1, 1′-binaphthyl, which is both bulky and electron-rich, as the ligand. A variety of amides, including aliphatic and aromatic primary amides, lactams, and carbamates, were viable substrates for the amidation, which exhibited good functional group compatibility. By tuning the substituents at the 2,2′-position of 1,1′-binaphthyl of the ligand, the palladium-catalyzed amidation of bulky aryl halides was realized and this coupling reaction was used to synthesize 2-amino-2′-methoxy-1,1′- binaphthyl in high yield.
Ma, Fangfang,Xie, Xiaomin,Zhang, Lei,Peng, Zhiyong,Ding, Lina,Fu, Lei,Zhang, Zhaoguo
experimental part
p. 5279 - 5285
(2012/08/07)

Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines
Microwave assisted simple, rapid, solventless, and catalyst-free chemoselective method for the protection of amino group in aromatic, aliphatic, heterocyclic, aralkyl amines, phenyl hydrazine, and amino acid esters in good to excellent isolated yield (83-98%) in short reaction time (2-12 min) has been reported.
Dighe, Satish N.,Jadhav, Hemant R.
p. 5803 - 5806
(2012/10/29)

Succinimide sulfonic acid (SuSA): An efficient and recyclable catalyst for the chemoselective N-Boc protection of amines
Succinimide sulfonic acid (SuSA) as a stable reagent is easily prepared by the reaction of succinimide with neat chlorosulfonic acid. This compound is able to catalyze the chemoselective conversion of amines to their corresponding N-Boc protected derivatives with (Boc)2O. All reactions were performed under mild conditions, giving the desired products in good to high yields. Springer-Verlag 2011.
Shirini, Farhad,Khaligh, Nader Ghaffari
experimental part
p. 631 - 635
(2012/07/03)

Poly(4-vinylpyridine) catalyzed chemoselective O-TMS protection of alcohols and phenols and N-Boc protection of amines
Poly(4-vinylpyridine) (PVP) acts as an efficient and reusable catalyst for the selective and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and N-tert-butoxycarbonylation of amines with (Boc)2O. All reactions were performed under mild conditions in good to high yields. Iranian Chemical Society 2012.
Shirini, Farhad,Khaligh, Nader Ghaffari
p. 495 - 502
(2013/02/22)

Total synthesis of argyrins A and e
The total synthesis of argyrins A and E were accomplished using a convergent strategy by condensation of one tripeptide and two dipeptide fragments. The synthesis strategy, which was developed for the protection of peptide fragments and identification of the optimum macrocylization site, can be applied to further synthetic studies involving other members of the argyrin family.
Wu, Wenbin,Li, Zheng,Zhou, Guangbiao,Jiang, Sheng
supporting information; experimental part
p. 2488 - 2491
(2011/05/09)

Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups
A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.
Jahani, Fatemeh,Tajbakhsh, Mahmood,Golchoubian, Hamid,Khaksar, Samad
supporting information; experimental part
p. 1260 - 1264
(2011/04/15)

Sulfonic acid-functionalized ordered nanoporous Na+- montmorillonite (SANM): A novel, efficient and recyclable catalyst for the chemoselective N-Boc protection of amines in solventless media
Sulfonic acid-functionalized ordered nanoporous Na+- montmorillonite (SANM) was used as an efficient catalyst for N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. No competitive side reactions such as isocyanate, urea, and N,N-di-Boc formation were observed. The reported method is mild, chemoselective and has the advantages such as heterogeneous catalysis, low cost and the recyclability of the catalyst.
Shirini, Farhad,Mamaghani, Manouchehr,Atghia, Seyyed Vahid
experimental part
p. 1088 - 1094
(2012/01/15)

Amination of aryl iodides using a fluorous-tagged ammonia equivalent
A fluorous-tagged ammonia equivalent for the Cu-catalyzed amination of aryl iodides is described in which N-Boc-protected anilines are produced in high overall yield and purity. All purification steps are performed using Fluorous SolidPhase Extraction (F-SPE) greatly simplifying and speeding up the isolation of the desired products.
Nielsen, Simon Dalsgaard,Smith, Garrick,Begtrup, Mikael,Kristensen, Jesper L.
experimental part
p. 3704 - 3710
(2010/09/05)

Pd-catalyzed amidation of aryl(Het) halides with tert-butyl carbamate
Pd-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs2CO3 as base in 1,4-dioxane as solvent was investigated, which resulted in the formation of the desired compounds in moderate to excellent yields.
Qin, Lijin,Cui, Hongmeng,Zou, Dapeng,Li, Jingya,Wu, Yangjie,Zhu, Zhiwu,Wu, Yusheng
experimental part
p. 4445 - 4448
(2010/09/12)

An expeditious, efficient green methodology for the Boc protection of amines and silyl protection of alcohols over tungstophosphoric acid-doped mesoporous silica
An efficient, chemoselective and eco-friendly protocol for the protection of amines as N-tert-butylcarbamate using (Boc)2O and protection of alcohols as silyl ether using HMDS over tungstophosphoric acid/SBA15 has been developed. Solventless condition, easy work-up, short reaction time, excellent yields and reusability of the catalyst are the striking features of this methodology which can be considered to be one of the better methods for the protection of amines and alcohols.
Karmakar, Bikash,Banerji, Julie
experimental part
p. 3855 - 3858
(2010/08/20)

Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile
Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst.
Zheng, Jianlong,Yin, Biaolin,Huang, Wenming,Li, Xiaopeng,Yao, Hequan,Liu, Zhaogui,Zhang, Jiancun,Jiang, Sheng
scheme or table
p. 5094 - 5097
(2009/12/01)

Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate
(Chemical Equation Presented) The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tertbutyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22°C) u
Bhagwanth, Swapna,Waterson, Alex G.,Adjabeng, George M.,Hornberger, Keith R.
supporting information; experimental part
p. 4634 - 4637
(2009/09/08)

Synthesis of chromanyl and dihydrobenzofuranyl piperazines
The synthesis of a series of regioisomeric chromanyl and dihydrobenzofuranyl piperazines is described.
Favor, David A.,Johnson, Douglas S.,Powers, James J.,Li, Tingsheng,Madabattula, Rambabu
p. 3039 - 3041
(2008/02/06)

Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature
Commercially available copper(II) tetrafluoroborate hydrate was found to be a highly efficient catalyst for chemoselective N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions and at room temperature. Various aromatic amines were protected as their N-tert-butyl carbamates in high yields and in short times. No competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation was observed. Chemoselective N-tert-butoxycarbonylation was achieved with substrates bearing OH and SH groups. Chiral α-amino acid esters afforded the corresponding N-t-Boc derivatives in excellent yields.
Chankeshwara, Sunay V.,Chakraborti, Asit K.
p. 1087 - 1091
(2007/10/03)

Synthesis of ring-A-substituted tryptophan by a palladium-catalyzed heteroannulation reaction
Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert- butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields. Georg Thieme Verlag Stuttgart.
Jia, Yanxing,Zhu, Jieping
p. 2469 - 2472
(2007/10/03)

A Lewis acid-mediated protocol for the protection of aryl amines as their Boc-derivatives
A new protocol of protection of poorly reactive aryl amines and functionalized amines with Boc2O in the presence of Zn(ClO 4)2·6H2O as the catalyst is reported. The catalytic action of Zn(ClO4)2·6H2O is specific for the activation of the pyrocarbonates, thus acid sensitive functionalities and stereochemical configurations of the starting materials remain unaltered in the protection process.
Bartoli, Giuseppe,Bosco, Marcella,Locatelli, Manuela,Marcantoni, Enrico,Massaccesi, Massimo,Melchiorre, Paolo,Sambri, Letizia
p. 1794 - 1798
(2007/10/03)

Remote Effects Modulating the Spin Equilibrium of the Resting State of Cytochrome P450cam - An Investigation Using Active Site Analogues
The crystal structure of the resting state of cytochrome P450 cam (CYP101), a heme thiolate protein, shows a cluster of six water molecules in the substrate binding pocket, one of which is coordinating to iron(III) as sixth ligand. The resting
Lochner, Martin,Mu, Linjing,Woggon, Wolf-D.
p. 743 - 765
(2007/10/03)

General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety
Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.
Kondo, Yoshinori,Kojima, Satoshi,Sakamoto, Takao
p. 6507 - 6511
(2007/10/03)

A Simple Method for the Protection of Aryl Amines as their t-Butylcarbamoyl (Boc) Derivatives
It has been found that aryl amines can be directly protected as their Boc derivatives by treatment of the amine with two equivalents of NaHMDS in THF followed by one equivalent of di-t-butyldicarbonate.This procedure works on a wide variety of both electron-rich and electron-deficient aryl amines.
Kelly, Terence A.,McNeil, Daniel W.
p. 9003 - 9006
(2007/10/02)