Month: November 2022

Thakur, Nimisha published the artcileEnantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5, COA of Formula: C4H11NOS, the main research area is chiral catalyst synthon enantioselective enantiomeric impurity; chiral separation; enantiomeric excess; enantiomeric impurity; enantioselective syntheses.

The enantiomeric excess of chiral starting materials is one of the important factors determining the enantiopurity of products in asym. synthesis. Fifty-one com. available chiral reagents used as building blocks, catalysts, and auxiliaries in various enantioselective syntheses were assayed for their enantiomeric purity. The test results were classified within five impurities level (ie, <0.01%, 0.01%-0.1%, 0.1%-1%, 1%-10%, >10%). Previously from 1998 to 2013, several reports have been published on the enantiomeric composition of more than 300 chiral reagents. This series of papers is necessitated by the fact that new reagents are forthcoming and that the enantiomeric purity of the same reagent can vary from batch to batch and/or from supplier to supplier. This report presents chiral liquid chromatog. (LC) and gas composition(GC) methods to sep. enantiomers of chiral compounds and evaluate their enantiomeric purities. The accurate and efficient LC anal. was done using newly introduced superficially porous particle (SPP 2.7μm) based chiral stationary phases (TeicoShell, VancoShell, LarihcShell-P, and NicoShell).

Chirality published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, COA of Formula: C4H11NOS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Li, Bowen published the artcileNickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines, Application In Synthesis of 343338-28-3, the main research area is asym hydrogenation sulfonyl imine nickel catalyst quinoxaline phosphine ligand; amines; asymmetric catalysis; hydrogenation; nickel; reaction mechanisms.

An efficient nickel-catalyzed asym. hydrogenation of N-tert-Bu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP*, I, as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asym. hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.

Angewandte Chemie, International Edition published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application In Synthesis of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

De Croos, Philomen published the artcileDevelopment of a Large-Scale Asymmetric Process for tert-Butanesulfinamide, Application In Synthesis of 343338-28-3, the main research area is butanesulfinamide enantioselective preparation.

Process development for a scalable and green synthesis of chiral tert-butanesulfinamide (TBSA) on a multikilogram scale is reported. The process is based on the identification of a chiral sulfinyl transfer agent, benzo[1,3]oxathiozin-2-one, that contains active and differentiated S-N and S-O bonds, allowing the synthesis to proceed under mild reaction conditions. This method is practical and overcomes the disadvantages of earlier methods deploying harsh reaction conditions and hazardous and toxic reagents.

Organic Process Research & Development published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application In Synthesis of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Hardouin, Christophe published the artcileMultikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 2. Manufacture of the 1,3-Diamine Moiety and Improvement of the Final Coupling Reaction, Category: amides-buliding-blocks, the main research area is acylsulfonamide diamine telescoped process aza Reformatsky coupling chemoselective amination.

This paper describes the synthesis of kilogram quantities of the sulfonamide moiety I involved in a coupling reaction with acid moiety II to provide batches of drug candidate III for preclin. studies and first-in-human clin. trials. A first approach relying on a chiral separation furnished the desired enantiomer of 1,3-diamine IV, precursor of sulfonamide I. An enantiomeric synthesis of IV using the Ellman’s chiral auxiliary coupled with an aza-Reformatsky reaction to control the stereochem. is also discussed. Coupling conditions of the final step involving EDCI to provide III under a cGMP process are detailed. An alternative approach using N-(1-methanesulfonyl)benzotriazole is also presented.

Organic Process Research & Development published new progress about Amination (chemoselective). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Category: amides-buliding-blocks.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Sedov, Igor published the artcileThe Gibbs free energy of cavity formation in a diverse set of solvents, HPLC of Formula: 123-39-7, the main research area is Gibbs energy cavity diverse set solvent.

The concept of the formation of a solute-sized cavity in a solvent is widely used in the theories of solvation processes; however, most of the studies of cavity formation using atomistic simulations were limited to water and hydrocarbon models. We calculated the Gibbs free energy of cavity formation ΔcavG for a structurally diverse set of 23 common organic solvents. For the calculation, mol. dynamics simulations of solvent boxes were conducted, and the Widom particle insertion method was applied. The results obtained with two different force fields for the same solvent were in good agreement with each other in most cases. The obtained cavity size dependences of ΔcavG allowed ranking the solvents by the free energy cost of creation of a cavity with a certain size. Surprisingly, this cost was somewhat higher in glycerol, formamide, and ethylene glycol than in water. In general, higher values of ΔcavG are observed for the solvents with a branched network of intermol. hydrogen bonds and strongly polar aprotic solvents. The numerical results can be used to improve the accuracy of the calculation of the cavity term in non-aqueous continuum solvation models. (c) 2020 American Institute of Physics.

Journal of Chemical Physics published new progress about Free energy (of cavitation). 123-39-7 belongs to class amides-buliding-blocks, name is N-Methylformamide, and the molecular formula is C2H5NO, HPLC of Formula: 123-39-7.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Ondachi, Pauline W. published the artcileSynthesis, Nicotinic Acetylcholine Receptor Binding, and in Vitro and in Vivo Pharmacological Properties of 2′-Fluoro-(substituted thiophenyl)deschloroepibatidine Analogues, Recommanded Product: 5-Bromothiophene-3-carboxamide, the main research area is nicotinic receptor binding fluoro thiophenyldeschloroepibatidine analog preparation nicotine dependence; in vitro/in vivo studies; nAChR antagonist; nicotine receptors; α4β2- and α3β4-nAChR.

The synthesis, nAChR in vitro and in vivo pharmacol. properties of 2′-fluoro-3′-(substituted thiophenyl)deschloroepibatidine analogs are presented herein. All had subnanomolar affinity at α4β2*-nAChRs. Contrary to lead structure epibatidine, a potent nAChR agonist, all were potent α4β2- and α3β4-AChR antagonists in an in vitro functional assay. In vivo, the compounds were also nAChR antagonists with various degrees of agonist activity. Many of the compounds had no agonist effects in the tail-flick, hot-plate, hypothermia, or spontaneous activity tests, whereas others did not have agonist activity in the tail-flick and hot-plate tests but like varenicline, were agonists in the hypothermia and spontaneous activity tests. Compound 4-(5-(7-azabicyclo[2.2.1]hept-2-yl)-2-fluoropyridin-3-yl)thiophene-2-carboxamide had agonist activity in all four in vivo tests. All the compounds were antagonists of nicotine-induced antinociception in the tail-flick test and most were antagonists of nicotine-induced antinociception in the hot-plate test. Compound 2-[5-(4-chlorothiophen-2-yl)-6-fluoropyridin-3-yl]-7-azabicyclo[2.2.1]heptane which had a Ki = 0.86 nM in the binding assay similar potency at α4β2/α3β4 with selectivity relative to α7 nAChRs, AD50 value of 0.001 μg/kg in the tail-flick test with no agonist activity in the in vitro or in vivo test had one of the more interesting profiles.

ACS Chemical Neuroscience published new progress about Drug dependence (treatment). 189329-94-0 belongs to class amides-buliding-blocks, name is 5-Bromothiophene-3-carboxamide, and the molecular formula is C5H4BrNOS, Recommanded Product: 5-Bromothiophene-3-carboxamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Kuznetsova, O. V. published the artcileCorrelation analysis of quantum chemical data and the polarizability effect in H-complexes, Synthetic Route of 359-38-6, the main research area is correlation quantum chem data polarizability effect hydrogen bonded complex.

The study is concerned with anal. of the energies of formation (E), frequency shifts (Δν) in IR spectra, ionization potentials (IP) of H-complexes, hydrogen bond lengths (r), and spin densities (sd) in H-complexes involving radical cations, obtained from quantum chem. calculations for 20 series of H-complexes. It was for the first time established that the E, IP, r, and sd values and the changes in enthalpy (δH) depend not only on the inductive and resonance effects but also on the polarizability effect of the substituents bound to the donor and acceptor centers in the H-complexes. Interrelations between the polarizability effect and the mol. structure of H-complexes are considered.

Russian Chemical Bulletin published new progress about Bond length (hydrogen bond). 359-38-6 belongs to class amides-buliding-blocks, name is 2,2-Difluoroacetamide, and the molecular formula is C2H3F2NO, Synthetic Route of 359-38-6.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Hornink, Milene M. published the artcileUltrasound-mediated radical cascade reactions: fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates, Quality Control of 123-39-7, the main research area is indoline acetamide methoxycarbonyl preparation green chem; acrylate arylaminomethyl ultrasound radical tandem addition cyclization formamide; Functionalized indolines; Indolines; Organic synthesis; Pulsed ultrasound; Sono-Fenton; Ultrasound.

Novel functionalized indolines were synthesized from 2-(((N-aryl)amino)methyl)acrylates and formamides under ultrasonic irradiation for the first time. Aiming to develop a straightforward and easy-to-implement methodol. for the synthesis of indolines, an instrumentation setup was designed, including ultrasound (US) equipment (Ultrasonic Horn; tip diameter of 12.7 mm, 20 kHz, maximum power of 400 W), an open reaction flask, and an inexpensive and green catalyst (1 mol%; FeSO4·7H2O) without the need for anhydrous conditions. The use of the sono-Fenton process in the presence of formamides and 2-(((N-aryl)amino)methyl)acrylates afforded a broad range of functionalized indolines within 60 s in high yields. Several exptl. parameters of the ultrasound-assisted reaction were evaluated, such as amplitude (40-80%), sonication time (15-60 s), and pulsed ultrasonic irradiation A 60 s silent reaction did not produce the desired indoline. The optimized conditions for US-mediated reactions allowed the production of functionalized indolines in high isolated yields (up to 99%, 60 s reaction time, pulse ratio 1 s:1 s, US amplitude 60%).

Ultrasonics Sonochemistry published new progress about Addition reaction catalysts. 123-39-7 belongs to class amides-buliding-blocks, name is N-Methylformamide, and the molecular formula is C2H5NO, Quality Control of 123-39-7.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Zhang, Ye published the artcileTotal Synthesis of (-)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade, Product Details of C4H11NOS, the main research area is chemoselective oxidation aza Achmatowicz rearrangement cyclization cascade diastereoselective; alstofolinine A total synthesis.

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asym. total synthesis of the macroline-type indole alkaloid (-)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives

Synlett published new progress about Achmatowicz reaction (aza-). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Product Details of C4H11NOS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Zhang, Lei published the artcileTotal Synthesis of (-)-Alstofolinine A through a Furan Oxidation/Rearrangement and Indole Nucleophilic Cyclization Cascade, Safety of (S)-2-Methylpropane-2-sulfinamide, the main research area is alstofolinine A total synthesis furan oxidation aza Achmatowicz rearrangement; oxidation rearrangement nucleophilic cyclization cascade azabicyclononane core preparation; aza-Achmatowicz rearrangement; furan; indole; natural-product synthesis; selective oxidation.

A reaction cascade of aza-Achmatowicz rearrangement followed by indole nucleophilic cyclization was developed to generate the common indole-fused azabicyclo[3.3.1]nonane core of the macroline family of alkaloids. The key to the success of the strategy relies on the careful manipulation of protecting groups and judicious selection of chemoselective furan oxidation conditions. The synthetic utility was further demonstrated on the asym. total synthesis of (-)-alstofolinine A (I). The compounds were evaluated for their antitumor activity using four cancer cell lines. Differential activities were observed, indicating that indole-containing multicyclic structures can exert potential and selective biomedical properties, justifying them as hit compounds worthy of further development.

Angewandte Chemie, International Edition published new progress about Achmatowicz reaction (aza-). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Safety of (S)-2-Methylpropane-2-sulfinamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics