Tag: 100-200

Category: esters-buliding-blocksIn 2021 ,《Process Development of a Second Generation β-Amyloid-Cleaving Enzyme Inhibitor-Improving the Robustness of a Halogen-Metal Exchange Using Continuous Stirred-Tank Reactors》 was published in Organic Process Research & Development. The article was written by Li, Bryan; Barnhart, Richard W.; Dion, Amelie; Guinness, Steven; Happe, Alan; Hayward, Cheryl M.; Kohrt, Jeffrey; Makowski, Teresa; Maloney, Mark; Nelson, Jade D.; Nematalla, Asaad; McWilliams, J. Christopher; Peng, Zhihui; Raggon, Jeffrey; Sagal, John; Weisenburger, Gerald A.; Bao, Denghui; Gonzalez, Miguel; Lu, Jiangping; McLaws, Mark D.; Tao, Jian; Wu, Baolin. The article contains the following contents:

Process development for the synthesis of a second generation β-amyloid-cleaving enzyme (BACE1) inhibitor is described. The lithiothiazole addition to the isoxazolene under batch conditions was not scalable because of reaction gelling and anion instability. A continuous stirred-tank reactor flow process was developed and successfully executed on the 70 kg scale in multiple runs. In a head-to-head comparison between the continuous and batch processes, the former was clearly superior as it gave a higher yield (80 vs 63%) of the (pyranoisoxazolyl)thiazole adduct and better reaction control for handling the unstable lithiothiazole as a reaction intermediate. Subsequently, (pyranoisoxazolyl)thiazole underwent Pd-catalyzed amination with t-Bu carbamate, reductive cleavage of the N-O bond, thioamidine cyclization, and deprotection of the Boc group to provide hydropyranothiazine. The synthesis of second generation β-amyloid-cleaving enzyme (BACE1) inhibitor was completed by amidation with 5-(difluoromethoxy)picolinic acid and the successive deprotection of the benzamide group with either Silicycle-diamine or L-lysine. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl carbamate(cas: 4248-19-5Category: esters-buliding-blocks)

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Category: esters-buliding-blocks

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

Application In Synthesis of Ethyl oxalyl monochlorideIn 2020 ,《Efficient separation of thorium from rare earth using oxamic acid in hydrochloric acid medium》 appeared in Separation and Purification Technology. The author of the article were Bie, Chao; Gao, Yun; Su, Jia; Dong, Yamin; Guo, Xiangguang; Sun, Xiaoqi. The article conveys some information:

Thorium (Th) is a promising element that can be converted to fissile uranium for nuclear energy. A large amount of slag containing Th need to be effectively treated and stacked in rare earth (RE) industry. It is of importance to develop some novel processes for separating Th from REs using solvent extraction The amide group was considered to have good selectivity for Th separation from REs. In order to solve the problem of RE entrainment during Th separation together with primary amine (N1923, (CnH2n+1)2CHNH2 n = 9-11) does not extract Th in hydrochloric acid system, three oxamic acid type extractants have been designed and synthesized in this paper. Among the extractants, the separation performance of 2-(dibenzylamino)-2-oxoacetic acid (DBOA) was indicated to be the best. As for the effective separation, the electron affinity of Th was larger, it was more preferred to coordinate with the extractant. The hydrogen ions released by the extractant could inhibit the extraction of REs rather than Th. Accordingly, Th could be separated from REs. Saponification process of oxamic acid extractant could be omitted in this separation process. By extracting Th using a lower concentration of oxamic acid selectively, not only the loss of RE could be reduced, but also a higher purity of Th could be obtained. Using a simplified fractional extraction experiment, the purity of RE in aqueous phase was increased to be 99.92% or higher, and the purity of obtained Th after stripping from loaded organic phase was increased to be 99.5%. After reading the article, we found that the author used Ethyl oxalyl monochloride(cas: 4755-77-5Application In Synthesis of Ethyl oxalyl monochloride)

Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.Application In Synthesis of Ethyl oxalyl monochloride

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

Recommanded Product: Ethyl 3-oxopentanoateIn 2019 ,《Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Yan, Zhongzhong; Liu, Aiping; Ou, Yingcan; Li, Jianming; Yi, Haibo; Zhang, Ning; Liu, Minhua; Huang, Lu; Ren, Jianwei; Liu, Weidong; Hu, Aixi. The article conveys some information:

Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC50 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, I gave the optimal fungicidal activity, which resp. offers control effects with EC50 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to com. fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound I has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future. In the experimental materials used by the author, we found Ethyl 3-oxopentanoate(cas: 4949-44-4Recommanded Product: Ethyl 3-oxopentanoate)

Ethyl 3-oxopentanoate(cas: 4949-44-4) belongs to ketone compounds. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids.Recommanded Product: Ethyl 3-oxopentanoate

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

On June 3, 2010, Mochizuki, Akiyoshi; Nagata, Tsutomu; Kishida, Masanori; Takano, Daisuke; Kanno, Hideyuki published a patent.Electric Literature of 114312-57-1 The title of the patent was Preparation of N-(2-acylaminobenzyl or 2-acylaminoheterocyclylmethyl)thiophene-2-carboxamide derivatives as antithrombotics. And the patent contained the following:

Diamides represented by the general formula [I; ring A = benzene, pyridine, pyridazine, pyrazine, or pyrimidine ring; R1 = H, halo, C1-6 alkyl, halo-C1-6 alkyl, HO, C1-6 alkoxy, halo-C1-6 alkoxy; R2 = H, halo, C1-6 alkyl, halo-C1-6 alkyl, HO, C1-6 alkoxy, halo-C1-6 alkoxy, C1-6 alkylsulfonyloxy, cyano, CO2H, C1-6 alkoxycarbonyl, carboxy-C1-6 alkyl, each (un)substituted CONH2 or NH2, , etc.; T1 = CONR3, NR3CO; R3 = H, C1-6 alkyl; T2 = CR4R5NHCO; R4, R5 = H, C1-6 alkyl; Q1 = C1-6 alkylsulfonylphenyl, N,N-di(C1-6 alkyl)aminocyclohexyl, 2-oxopyrrolidinyl, 2-oxo[1,3]oxazolidinyl, 1,1-dioxo-1λ6-isothiazolidinyl, 1-C1-6 alkylpiperidinyl, etc.; Q2 = a single bond, (un)substituted 1,4-phenylene, piperidine-1,4-diyl, thiazole-2,5-diyl, [1,3,4]thiadiazole-2,5-diyl, pyridine-2,5-diyl; Q3 = each (un)substituted Ph, thienyl, pyrrolyl, or pyridyl] or pharmacol. acceptable salts thereof were prepared These compounds have a potent inhibitory activity on activated blood coagulation factor Xa (FXa) and exhibit quick, sufficient and lasting antithrombotic effect even by oral administration. They are useful for the prevention and/or treatment of thrombus or embolism, more specifically cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary embolism, Buerger disease, deep vein thrombosis, disseminated intravascular coagulation (DIC), thrombus formation after artificial valve/joint replacement, thrombus formation or re-obstruction (clogging) after vascular reconstruction, multiple organ failure (MODS), thrombus formation during extracorporeal circulation, or blood coagulation during blood sampling. Thus, 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride 260, HOBt 140, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 234 mg, and 320 μL Et3N were added to a solution of 253 mg N-(2-aminobenzyl)-5-chlorothiophene-2-carboxamide in 10 mL DMF and the resulting mixture was stirred at room temperature for 23 h to give, after workup, 262 mg N-[2-[[[(5-Chlorothiophen-2-yl)carbonyl]amino]methyl]phenyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide (II). II hydrochloride and 4-[[[(5-Chlorothiophen-2-yl)carbonyl]amino]methyl]-3-fluoro-5-[[(5-isopropyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino]benzoic acid Me ester (III) inhibited human FXa with IC50 of 1.7 and 0.51 nM, resp. The experimental process involved the reaction of Ethyl 3-fluoro-2-methylbenzoate(cas: 114312-57-1).Electric Literature of 114312-57-1

The Article related to angina pectoris, anticoagulants, brain infarction, diamides role: pac (pharmacological activity), spn (synthetic preparation), thu (therapeutic use), biol (biological study), prep (preparation), uses (uses), disseminated intravascular blood coagulation, embolism, homo sapiens, human, multiple organ failure, myocardial infarction, pulmonary embolism, stroke, thromboangiitis obliterans, thrombus, venous thrombosis and other aspects.Electric Literature of 114312-57-1

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

On November 25, 1997, Berryman, Kent Alan; Doherty, Annette Marian; Edmunds, Jeremy John; Patt, William Chester; Plummer, Mark Stephen; Repine, Joseph Thomas published a patent.Quality Control of Methyl 2-(3-formylphenyl)acetate The title of the patent was Preparation of 3,5-diphenyl-2(5H)-furanone derivatives as nonpeptide endothelin I antagonists. And the patent contained the following:

Novel nonpeptide antagonists of endothelin I represented by formula [I; R1 = (un)substituted C3-12 cycloalkyl, Ph substituted with 1-5 substituents, naphthyl or heteroaryl optionally substituted with 1-5 substituents; R2 = C1-12 linear or branched alkyl, C3-12 linear or branched cycloalkyl, aryl optionally substituted with 1-5 substituents, heteroaryl optionally substituted with 1-3 substituents; R3 = (un)substituted C1-12 linear or branched alkyl, (un)substituted C3-12 cycloalkyl, aryl optionally substituted with 1-5 substituents, heteroaryl optionally substituted with 1-3 substituents; R4 = OH, OR5, (CH2)nOR5; wherein R5 = (un)substituted C1-7 alkyl; X = O, S] or tautomeric open chain keto-acids forms thereof or pharmaceutically acceptable salt thereof are prepared Also described are pharmaceutical compositions of the above compounds, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, myocardial ischemia, cerebral vasospasm, cerebral ischemia, cerebral infarction, cirrhosis, septic shock, congestive heart failure, endotoxic shock, subarachnoid hemorrhage, arrhythmia, asthma, preeclampsia, atherosclerotic disorders including Raynaud’s disease and restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, hemorrhagic shock, ischemic bowel disease, stroke, benign prostatic hyperplasia (BPH), and diabetes. Thus, Me 2-benzoyl-2-phenylacetate derivative (II) and 3,4,5-trimethoxybenzladehyde were refluxed in the presence of NaOMe in MeOH for 18 h and the solution was treated with AcOH and refluxed an addnl. 72 h, followed by saponification of the product with 1N aqueous NaOH and acidification to give 28% I (X = O, R1 = Q, R2 = 3,4,5-trimethoxyphenyl, R3 = 4-methoxyphenyl, R4 = OH). The latter compound in vitro showed an antagonism of endothelin I-stimulated vasoconstriction in the rabbit femoral artery and sarafotoxin 6c-stimulated vasoconstriction in the rabbit pulmonary artery with pA2 values of 0.00025 and 0.34, resp. The experimental process involved the reaction of Methyl 2-(3-formylphenyl)acetate(cas: 142327-44-4).Quality Control of Methyl 2-(3-formylphenyl)acetate

The Article related to acute renal failure, angina pectoris, antiarrhythmics, antiasthmatics, antiatherosclerotics, antidiabetic agents, antihypertensives, antitumor agents, benign prostatic hyperplasia, brain infarction, brain ischemia, cerebral artery spasm, chronic renal failure, cirrhosis, coronary restenosis, gastric mucosa (damage), heart failure and other aspects.Quality Control of Methyl 2-(3-formylphenyl)acetate

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

In 2019,Chemistry – A European Journal included an article by Gonzalez, Maria J.; Breit, Bernhard. Related Products of 2495-35-4. The article was titled 《Visible-Light-Driven Intermolecular Reductive Ene-Yne Coupling by Iridium/Cobalt Dual Catalysis for C(sp3)-C(sp2) Bond Formation》. The information in the text is summarized as follows:

A new methodol. to form C(sp3)-C(sp2) bonds by visible-light-driven intermol. reductive ene-yne coupling was successfully developed. The process relied on the ability of the Hantzsch ester to contribute in both SET and HAT processes through a unified cobalt and iridium catalytic system. This procedure avoided the use of stoichiometric amounts of reducing metallic reagents, which was translated into high functional-group tolerance and atom economy. After reading the article, we found that the author used Benzyl acrylate(cas: 2495-35-4Related Products of 2495-35-4)

Benzyl acrylate(cas: 2495-35-4) has been used in preparation of high refractive index polyacrylates. Benzyl acrylate is used in the preparation of heptanoic acid benzyl ester. It is used to prepare polybenzylacrylate using azobisisobutyronitrile as initiator.Related Products of 2495-35-4

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

In 2017,Goldstein, Steven W.; Bill, Ashley; Dhuguru, Jyothi; Ghoneim, Ola published 《Nucleophilic Aromatic Substitution-Addition and Identification of an Amine》.Journal of Chemical Education published the findings.Electric Literature of C8H6FNO4 The information in the text is summarized as follows:

The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chem. arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the m.p. and 1H NMR spectrum of the product. In the experiment, the researchers used many compounds, for example, Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Electric Literature of C8H6FNO4)

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Electric Literature of C8H6FNO4Methyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

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

In 2014,Tamiaki, Hitoshi; Isoda, Yasuaki; Tanaka, Takuya; Machida, Shinnosuke published 《Synthesis of chlorophyll-amino acid conjugates as models for modification of proteins with chromo/fluorophores》.Bioorganic & Medicinal Chemistry published the findings.Safety of Methyl 3-hydroxypropanoate The information in the text is summarized as follows:

A chlorophyll-a derivative bonded directly with epoxide at the peripheral position of the chlorin π-system was reacted with N-urethane and C-ester protected amino acids bearing an alc. or phenolic hydroxy group as well as a carboxy group at the residue to give chlorophyll-amino acid conjugates. The carboxy residues of N,C-protected aspartic and glutamic acids were esterified with the epoxide in high yields. The synthetic conjugates in dichloromethane had absorption bands throughout the visible region including intense red-side Qy and blue-side Soret bands. By their excitation at the visible bands, strong and efficient fluorescence emission was observed up to the near-IR region. The chromo/fluorophores are promising for preparation of functional peptides and modification of proteins. In the experimental materials used by the author, we found Methyl 3-hydroxypropanoate(cas: 6149-41-3Safety of Methyl 3-hydroxypropanoate)

Methyl 3-hydroxypropanoate(cas: 6149-41-3) belongs to esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Safety of Methyl 3-hydroxypropanoate

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

Zhang, Qi; Li, Yao; Zhang, Long; Luo, Sanzhong published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Catalytic Asymmetric Disulfuration by a Chiral Bulky Three-Component Lewis Acid-Base》.Application of 609-14-3 The article contains the following contents:

A three-component Lewis acid-base (Lewis trio) involving a bulky chiral primary amine, B(C6F5)3 and a bulky tertiary amine has been developed as an effective enamine catalyst for enantioselective disulfuration reactions. The bulky tertiary amine was found to activate a bulky primary-tertiary diamine-borane Lewis pair for enamine catalysis via frustrated interaction. The resulted chiral bulky Lewis trio (BLT) allows for the construction of chiral disulfides via direct disulfuration with β-ketocarbonyls or α-branched aldehydes in a practical and highly stereocontrolled manner. After reading the article, we found that the author used Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3Application of 609-14-3)

Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3) belongs to ketone compounds. Ketones are highly reactive, although less so than aldehydes, to which they are closely related. Much of their chemical activity results from the nature of the carbonyl group. Ketones readily undergo a wide variety of chemical reactions.Application of 609-14-3

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

Rashed, Nurnobi Md.; Masuda, Koichiro; Ichitsuka, Tomohiro; Koumura, Nagatoshi; Sato, Kazuhiko; Kobayashi, Shu published their research in Advanced Synthesis & Catalysis in 2021. The article was titled 《Zirconium Oxide-Catalyzed Direct Amidation of Unactivated Esters under Continuous-Flow Conditions》.Quality Control of Methyl 4-fluorobenzoate The article contains the following contents:

A sustainable and environmentally benign direct amidation reaction of unactivated esters with amines was developed in a continuous-flow system. A com. available amorphous zirconium oxide was found to be an efficient catalyst for this reaction. While the typical amidation of esters with amines required a stoichiometric amount of a promoter or metal activator, the present continuous-flow method enabled the direct amidation reaction under additive-free conditions with an extensive diversity towards various functional groups. High yields of the products were obtained with a nearly equimolar proportion of starting materials to reduce byproduct formation, which rendered this process applicable for use in a sequential-flow system. The experimental process involved the reaction of Methyl 4-fluorobenzoate(cas: 403-33-8Quality Control of Methyl 4-fluorobenzoate)

Methyl 4-fluorobenzoate(cas: 403-33-8) is an organic fluorinated building block used for the synthesis of various pharmaceutical compounds. It can be used for the preparation of Blonanserin.Quality Control of Methyl 4-fluorobenzoate

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