- Formation and verification of the structure of the 1-fluorenylmethyl chloroformative derivative of sulfamethazine
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Sulfamethazine (SMZ) is derivatized with 1-fluorenylmethyl chloroformate (FMOC) to form the fluorescent adduct SMZ-FMOC. Conditions for formation are optimized with respect to pH, reagent concentration, and reagent ratio. Reagent and product profiles (including the hydrolysis byproduct FMOC-OH) versus time are followed by reversed phase HPLC with UV absorbance detection. FMOC-SMZ has been crystallized, its composition confirmed by microanalysis, and its structure corroborated by IR and NMR spectroscopy. From 10 down to 1 ppm, there is clear gentle curvature in the fluorescence intensity of SMZ-FMOC. The linear response range extends from above 100 ppb down to about 100 ppt, and an increase in sensitivity for the fluorescent detection of FMOC-SMZ (over the usual UV absorbance detection of SMZ) is calculated to be better than 3 orders of magnitude.
- Liang,Zhang,Baker,Cross
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Read Online
- Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives
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The shortest synthesis of N-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of tert-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.
- Erb, William,Levanen, Gael,Roisnel, Thierry,Dorcet, Vincent
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Read Online
- SAR of novel biarylmethylamine dopamine D4 receptor ligands
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SAR for a novel series of dopamine D4 receptor ligands is shown. Very selective, highly potent compounds like 1-(2-pyrimidinyl)-4-(3-(3-thienyl)- benzyl)-piperazine (5f) and 2-(4-(1-fluorenylmethyl)-1-piperazinyl)- pyrimidine (8c) were obtained.
- Arlt, Michael,Boettcher, Henning,Riethmueller, Angelika,Schneider, Guenter,Bartoszyk, Gerd D.,Greiner, Hartmut,Seyfried, Christoph A.
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Read Online
- Me3SI-promoted chemoselective deacetylation: a general and mild protocol
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A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.
- Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
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p. 19310 - 19315
(2021/06/03)
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- Method for high-selectivity synthesis of 9-fluorenylcarbinol
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The invention discloses a method for high-selectivity synthesis of 9-fluorenylcarbinol. The method comprises the following steps: heating and dissolving fluorene in a DMSO solvent system at 50-55 DEG C in the presence of a sodium ethoxide ethanol solution alkali catalyst, adding an acylation reagent ethyl formate, carrying out acylation reaction at the same temperature to prepare 9-fluorenylformaldehyde, adding a soluble metal inorganic salt auxiliary agent, then using NaBH4 for a reduction reaction, adjusting the pH value of reaction liquid to be neutral, and separating out 9-fluorene methanol solid sediment. According to the method disclosed by the invention, fluorene is completely converted by utilizing a section of temperature, the 9-fluorene methanol can be obtained through high-selectivity reduction without solvent conversion by adding the soluble metal inorganic salt auxiliary agent, and the yield of the 9-fluorene methanol is improved on the premise of shortening the reaction time.
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Paragraph 0025-0080
(2021/06/06)
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- Preparation method of 9-hydroxymethyl-fluorene diacid
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The invention provides a method for preparing 9-hydroxymethyl-fluorene diacid. The method comprises the following steps: (1) subjecting fluorene to reacting with paraformaldehyde to generate 9-hydroxymethylfluorene; (2) enabling the 9-hydroxymethylfluorene to react with acetyl chloride to generate (2,7-diacetyl-9H-fluoren-9-yl)methyl acetate; (3) enabling the (2,7-diacetyl-9H-fluoren-9-yl)methyl acetate to react with bromine to generate (2,7-bis(2,2-dibromoacetyl)-9H-fluoren-9-yl)methyl acetate; (4) enabling the(2,7-bis(2,2-dibromoacetyl)-9H-fluoren-9-yl)methyl acetate to react with bromine and sodium carbonate to generate 9-(acetoxymethyl)-9H-fluorene-2,7-dicarboxylic acid; and (5) subjecting 9-(acetoxymethyl)-9H-fluorene-2,7-dicarboxylic acid to reacting with an acidic solution to generate 9-hydroxymethyl-fluorene diacid. The method has the advantages of simple preparation process, accessible raw materials and high yield, and lowers the production cost of 9-hydroxymethyl-fluorene diacid.
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Paragraph 0039-0045; 0062-0063; 0068-0069; 0074-0075
(2020/12/10)
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- KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
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A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
- Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
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supporting information
p. 16702 - 16707
(2020/10/27)
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- Additive-free cobalt-catalysed hydrogenation of carbonates to methanol and alcohols
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Reduction of various organic carbonates to methanol and alcohols can be achieved in the presence of a molecularly-defined homogeneous cobalt catalyst. Specifically, the use of Co(BF4)2 in combination with either commercial or tailor-made tridentate phosphine ligands allows for additive-free hydrogenations of carbonates. Optimal results are obtained at relatively mild conditions (120 °C, 50 bar hydrogen pressure) in the presence of xylyl-Triphos L4.
- Ferretti, Francesco,Scharnagl, Florian Korbinian,Dall'Anese, Anna,Jackstell, Ralf,Dastgir, Sarim,Beller, Matthias
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p. 3548 - 3553
(2019/07/10)
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- Fmoc-OPhth, the reagent of Fmoc protection
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Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.
- Yoshino, Ryo,Tokairin, Yoshinori,Kikuchi, Mari,Konno, Hiroyuki
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supporting information
p. 1600 - 1603
(2017/04/03)
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- Preparation and characterization of a RHA/TiO2 nanocomposite: Introduction of an efficient and reusable catalyst for chemoselective trimethylsilyl protection and deprotection of alcohols and phenols
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In this work, rice husk ash (RHA), as a natural source of amorphous silica, was used as a support for the synthesis of anatase-phase titania nanoparticles leading to the RHA/TiO2 nanocomposite. This nanocomposite was used as an efficient catalyst for the chemoselective trimethylsilylation of various alcohols and phenols and deprotection of the obtained trimethylsilyl ethers. The procedure gave the products in excellent yields in very short reaction times. Also this catalyst can be reused at least six times without loss of its catalytic activity.
- Seddighi, Mohadeseh,Shirini, Farhad,Goli-Jolodar, Omid
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p. 23564 - 23570
(2016/03/12)
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- Introduction of PEG-SANM nanocomposite as a new and highly efficient reagent for the promotion of the silylation of alcohols and phenols and deprotection of the silyl ethers
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Poly (ethylene glycol)-sulfonated sodium montmorillonite (PEG-SANM) nanocomposite was prepared by a simple method and characterized using XRD, TGA, SEM, TEM, and FT-IR techniques. After preparation and characterization, this reagent was used as a highly efficient and reusable solid acid catalyst for the chemoselective silylation of alcohols and phenols and deprotection of the obtained silyl ethers. Themethod offers several advantages including high to excellent yields of the products, short reaction times, easy preparation of the catalyst and easy work-up procedure. In addition, the catalyst can be recycled and reused at least for five times without significant decrease in the catalytic activity.
- Shirini, Farhad,Shojaei, Abdollah Fallah,Heirati, Seyedeh Zahra Dalil
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p. 944 - 951
(2016/07/06)
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- An efficient synthesis of tert-butyl ethers/esters of alcohols/amino acids using methyl tert-butyl ether
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A facile synthesis of a wide variety of tert-butyl ethers and tert-butyl ester derivatives under mild conditions is described. Alcohols etherified with tert-butyl methyl ether as tert-butyl source and solvent, in the presence of sulfuric acid. Many amino acid tert-butyl esters have been synthesized by this procedure. The reaction is simple, inexpensive, easily scaled up, and proceeds without observable racemization. A green method was developed for the deprotection of this group using Amberlite resin IR 120-H as catalyst.
- Mallesha,Prahlada Rao,Suhas,Channe Gowda
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experimental part
p. 641 - 645
(2012/02/15)
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- Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
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Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
- Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
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- Nanocrystalline TiO2-HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols, phenols and deprotection of silyl ethers
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TiO2-HClO4, as a new solid acid, was found to be an efficient catalyst for the chemoselective trimethylsilylation of alcohols and phenols. Deprotection of the resulting trimethylsilylethers was achieved using the same catalyst in methanol solvent. The synthesized catalyst was characterized by FT-IR, SEM, TEM, BET and XRD analyses. Our novel synthetic method has the advantages of high yields, short reaction times, low cost and recyclability of the catalyst, simplicity and easy work-up compared to the conventional methods reported in the literature.
- Shirini, Farhad,Atghia, Seyyed Vahid,Jirdehi, Mojtaba Ghazi
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- InBr3-catalyzed deoxygenation of carboxylic acids with a hydrosilane: Reductive conversion of aliphatic or aromatic carboxylic acids to primary alcohols or diphenylmethanes
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A simple and practical procedure for the direct reduction of aliphatic carboxylic acids with a variety of functional groups to a primary alcohol using the mild reducing reagent tetramethyldisiloxane (TMDS), in the presence of a catalytic amount of InBr3 has been developed. This simple reducing system, when used together with a hydrosilane, allows the preparation of the diphenylmethane derivative directly from an aromatic carboxylic acid and an aromatic compound. Copyright
- Sakai, Norio,Kawana, Keita,Ikeda, Reiko,Nakaike, Yumi,Konakahara, Takeo
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experimental part
p. 3178 - 3183
(2011/06/28)
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- Chemoselective chemical and electrochemical deprotections of aromatic esters
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Alcohols can be easily and chemoselectively deprotected from the corresponding aromatic esters by using either SmI2/HMPA or by electrolysis In the presence of a proton source.
- Lam, Kevin,Marko, Istvan E.
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experimental part
p. 2752 - 2755
(2009/11/30)
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- Toluates: unexpectedly versatile reagents
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The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted.
- Lam, Kevin,Markó, István E.
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experimental part
p. 10930 - 10940
(2010/02/28)
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- Base Multiplying Agents and Base-Reactive Curable Compositions
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To provide such a base multiplying agent capable of being used for crosslinking reaction, for example of a epoxy compound and the like, that generates another base by action of a base, and can efficiently perform base multiplying reaction, and a base-reactive curable composition using the base multiplying agent. The base generating agent of the invention is represented by the following formula (1): (In the formula (1), X represents a hydrogen atom, a substituted alkyl group or an unsubstituted alkyl group; Y represents a substituted or unsubstituted alkylene chain; and n represents an integer of from 1 to 4.)
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Page/Page column 7
(2008/12/08)
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- Vanadium hydrogen sulfate (I): Chemoselective trimethylsilylation of alcohols and deprotection of trimethylsilyl ethers
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Trimethylsilylation of alcohols with hexamethyldisilazane (HMDS) catalyzed by V(HSO4)3 under mild and completely heterogeneous reaction condition is reported. The method is highly chemoselective for the protection of alcohols in the presence of phenols, amines and thiols. Also, the deprotection of trimethylsilyl ethers is performed in the presence of V(HSO 4)3 at room temperature in good to high yields.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh,Sakhaei, Ali Reza
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experimental part
p. 943 - 946
(2009/12/24)
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- Hydroxylation of Alkyl Halides with Water in Ionic Liquid: Significantly Enhanced Nucleophilicity of Water
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A facile method for the nucleophilic hydroxylation of alkyl halides and mesylates with water has been developed in which the use of ionic liquid as an alternative reaction medium not only enhanced the nucleophilicity of water but also reduced the formation of elimination products predominantly formed under the conventional basic reaction conditions. For example, hydroxylation of model compound 2-(3-bromopropyl)naphthalene (1) to 2-(3-hydroxypropyl)-naphthalene (2) with water in 1-n-butyl-3-methylimidazolium tetrafluoroborate ([bmim] [BF 4]) and 1,4-dioxane proceeded selectively in high yield (94%). The reactivity of other nucleophilic oxygen sources such as alcohol, phenol, and acetic acid in an ionic liquid was also investigated.
- Kim, Dong Wook,Hong, Dong Jin,Seo, Jai Woong,Kim, Hoon Sik,Kim, Hong Kon,Song, Choong Eui,Chi, Dae Yoon
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p. 3186 - 3189
(2007/10/03)
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- Low-temperature heat capacity and standard molar enthalpy of formation of 9-fluorenemethanol (C14H12O)
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Low-temperature heat capacities of the 9-fluorenemethanol (C 14H12O) have been precisely measured with a small sample automatic adiabatic calorimeter over the temperature range between T = 78 K and T = 390 K. The solid-liquid phase transition of the compound has been observed to be Tfus = (376.567 ± 0.012) K from the heat-capacity measurements. The molar enthalpy and entropy of the melting of the substance were determined to be ΔfusHm = (26.273 ± 0.013) kJ · mol-1 and ΔfusSm = (69.770 ± 0.035) J · K-1·mol-1. The experimental values of molar heat capacities in solid and liquid regions have been fitted to two polynomial equations by the least squares method. The constant-volume energy and standard molar enthalpy of combustion of the compound have been determined, ΔcU(C14H 12O, s) = -(7125.56 ± 4.62) kJ·mol-1 and ΔcHm°(C14H12 O, s) = -(7131.76 ± 4.62) kJ · mol-1 by means of a homemade precision oxygen-bomb combustion calorimeter at T = (298.15 ± 0.001) K. The standard molar enthalpy of formation of the compound has been derived, Δf Hm°(C14H 12 O, s) = -(92.36 ± 0.97) kJ · mol-1, from the standard molar enthalpy of combustion of the compound in combination with other auxiliary thermodynamic quantities through a Hess thermochemical cycle.
- Di, You-Ying,Tan, Zhi-Cheng,Sun, Xiao-Hong,Wang, Mei-Han,Xu, Fen,Liu, Yuan-Fa,Sun, Li-Xian,Zhang, Hong-Tao
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- V2O5-H2O2: A convenient reagent for the direct oxidation of acetals to esters
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Both cyclic and acyclic acetals were deprotected to give the corresponding aldehydes in acetonitrile, and are transformed to methyl esters in methanol, on treatment with a catalytic quantity of V2O5 and H2O2. Under identical conditions acid-sensitive alcohol protecting groups, such as tetrahydropyranyl and tert-butyldimethylsilyl ethers, were cleaved regenerating the corresponding alcohols.
- Gopinath, Rangam,Paital, Alok Ranjan,Patel, Bhisma K
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p. 5123 - 5126
(2007/10/03)
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- Tetrabutylammonium tribromide (TBATB)-promoted tetrahydropyranylation/depyranylation of alcohols
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Alcohols are tetrahydropyranylated rapidly in high yields in the presence of a catalytic amount of TBATB in dichloromethane at room temperature. Depyranylation to their parent alcohol is achieved in quantitative yields by merely changing the solvent to methanol.
- Naik, Sarala,Gopinath, Rangam,Patel, Bhisma K
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p. 7679 - 7681
(2007/10/03)
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- Protected compound comprising a protective group removably attached to a compound to be protected
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The protective group having the following formula (I): wherein Ar represents a substantially planar, fused ring system containing at least 4 aromatic rings, and L represents a group containing at least one carbon atom which is capable of bonding to a group to be protected.
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- Stepwise and concerted solvolytic elimination and substitution reactions: E1 reaction via a primary carbocation
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Solvolysis of 9-(X-methyl)fluorene (1-X, X = I, Br, OBs) in 25 vol % acetonitrile in water gives the elimination product 9- methylidenefluorene and the substitution products 9- (hydroxymethyl)fluorene (1-OH) and 9-(acetamidomethyl)fluorene (1- NHCOMe). Kinetic studies of the corresponding ring-substituted compounds 2-X and 3-X show that the rate of elimination increases with increasing acidity of the substrate, Bronsted α > 0. The small kinetic deuterium isotope effects measured for the elimination reactions of the brosylates 1-OBs and 3-OBs, k(H)/k(D) = 2.0 ± 0.1 and 2.8 ± 0.1, respectively, suggest significant amounts of E1 reaction. The bimolecular reactions of the brosylates with added bases may be of irreversible E1cB type in contrast to the reactions of the halides which exhibit E2 reaction with added bases as well as with solvent water.
- Meng, Qingshui,Thibblin, Alf
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p. 4834 - 4840
(2007/10/03)
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- An expedient preparation of 9-fluoronylmethanol
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Lithiation of fluorene in tetrahydrofuran with butyllithium followed by reaction with paraformaldehyde provides a convenient one-pot preparation (~70% isolated yield) of 9-fluorenylmethanol. The yield of 9-fluorenylmethanol is critically dependent on stoichiometry and reaction times.
- Chong,Lajoie,Tjepkema
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p. 819 - 820
(2007/10/02)
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- SIMULTANEOUS USE OF N-Fmoc AND OTmse PROTECTIVE GROUPS IN THE SYNTHESIS OF PEPTOLYTIC SENSITIVE PEPTIDES
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The combined use of Fmoc (fluorenylmethoxycarbonyl) as N-protection and Tmse (trimethylsilylethyl) as O-protection during demanding fragment condensation mediated by Bop-Cl (N,N'-bis(3-oxo-2-oxazolidinyl)phosphinyl chloride) has been explored in the preparation of useful synthons that are sensitive to acidic and even basic hydrolyses.Stepwise deprotection by morfoline (Fmoc-deprotection) followed by F--mediated removal of Tmse results in a very effective peptide synthesis strategy, as exemplified by the preparation of i.a.Phg-MePhe-Thz.Similarly, combinations of N-Boc, O-Tmse peptide esters are also possible that allow the preparation of +H2-MePhe-Thz-OTmse (via Boc-MePhe-Thz-OTmse) without competitive DKP formation.
- Vanfleteren, L.,Anteunis, M. J. O.
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p. 505 - 518
(2007/10/02)
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- A NOVEL DOUBLE DEPROTECTION-PEPTIDE CYCLISATION PROCEDURE AND ITS APPLICATION TO THE SYNTHESIS OF ANALOGUES OF THE CYCLIC TETRAPEPETIDE HC-TOXIN.
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A hydroxy-mediated Fmoc/methyl ester double deprotection procedure followed by an improved bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) cyclisation reaction are reported.This novel methodology was applied to the synthesis of three new HC-toxin analogues.
- Shute, Richard E.,Rich, Daniel H.
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p. 3419 - 3422
(2007/10/02)
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- GENERAL METHOD FOR THE PHOTOGENERATION OF BENZOLATED CATIONIC AND ANIONIC SYSTEMS IN AQUEOUS SOLUTION. TEST OF RELATIVE STABILITY OF THESE SYSTEMS IN THE EXCITED STATE.
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A general method for the photogeneration of dibenzolated carbocations and carbanions is described with the aim of testing the relative stability of these species as a function of number of pi-electrons in the excited state.
- Krogh, Erik,Wan, Peter
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p. 823 - 826
(2007/10/02)
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- CHEMISTRY AND KINETICS OF ARYL CARBENES IN METHANOL AT LOW TEMPERATURES.
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The chemistry and kinetics of six aryl carbenes in polycrystalline methanol are reported. The kinetics were monitored by triplet ESR spectroscopy. Isotope effects were used heavily to probe reaction mechanisms. Several analogues to solution chemistry and kinetics were found. It is concluded that the singlet-triplet energy separation decreases as DBS greater than DPC greater than DBT greater than NC greater than Fl greater than DMA.
- Wright,Platz
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p. 4175 - 4180
(2007/10/02)
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- Studies of the Borderline between Concerted and Stepwise Mechanisms of Elimination : E1cB Elimination of Fluoren-9-ylmethyl Carboxylate Esters
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Rates of β-elimination of carboxylate leaving groups from fluoren-9-ylmethyl carboxylate esters in methanolic sodium methoxide at 25 deg C are reported.An E1cB mechanism with rate-determining formation of a carbanion intermediate is assigned on the basis of near identity of measured elimination rates and rates of carbanion formation predicted from a Taft correlation, and the similarity with elimination of 1-(1-acetoxy-1-methylethyl)indene for which the mechanism has been established by Ahlberg and Thibblin.Values of ρ=0.42 and βlg=0.27 measured for substituted benzoate leaving groups are a little larger than expected (ca. 0.24 and 0.18, respectively) and the discrepancy is tentatively ascribed to conformational enhancement of remote substituent effects, rather than to a contribution of E2 elimination.The effects of alkyl and aryl substitution α to the leaving group are discussed, especially in relation to the borderline between concerted and stepwise mechanisms.The measurements fail to confirm an earlier inference that the borderline shows a discontinuity in transition-state structure at the point of mechanistic change.
- O'Ferrall, Rory A. More,Larkin, Finbar,Walsh, Peter
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p. 1573 - 1580
(2007/10/02)
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