Tag: M.W=300-400

581065-95-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 581065-95-4 as follows.

The preparation of compound D is disclosed in Cheng et al. 2013 (compound 108, FIG. 19). The preparation of compound E is disclosed in Cong et al. 2015 (compound 21, FIG. 2b). Compound F was prepared from tert-butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate (CAS Reg. No. 581065-95-4) by treatment with Fmoc-Cl to attach the Fmoc protecting group, followed by treatment with trifluoroacetic acid to cleave the t-butyl ester.

According to the analysis of related databases, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Young, Ian S.; Lou, Sha; Gangwar, Sanjeev; (16 pag.)US2019/388553; (2019); A1;,
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Adding some certain compound to certain chemical reactions, such as: 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18013-97-3. 18013-97-3

To the crude was added anhydrous Lambda/,/V-dimethylformamide (100 cm3), 2,5-dibromo-terephthalic acid diethyl ester (1 1 .0 g, 29 mmol) and bis(triphenylphosphine)palladium(ll) dichloride (612 mg, 0.87 mmol) and the mixture heated at 100 C for 2 hours. The mixture allowed to cool to 23 C, concentrated in vacuo and passed through a plug of silica (dichloromethane) to give a solid which was triturated in methanol. The solid collected by filtration to give 2,5-bis-thieno[2,3-b]thiophen-2-yl- terephthalic acid diethyl ester (1 1 .68 g, 81 %) as a yellow solid. 1H-NMR (400 MHz, CDCIs) 1 .13 (6H, t, J 7.1 ), 4.24 (4H, q, J 7.1 ), 7.24 (2H, d, J 5.2), 7.26 (2H, s), 7.37 (2H, d, J 5.2), 7.88 (2H, s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Diethyl 2,5-dibromoterephthalate.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
Ester – Wikipedia,
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A common compound: 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 18013-97-3

Under nitrogen protection,Diethyl 2,5-dibromoterephthalate (2g, 5.26mmol), compound 1 (7.03, 13.68mmol), and dry toluene (40mL) were added to a 100mL two-necked flask, and nitrogen was bubbled through to remove it. After half an hour of oxygen, Pd (PPh3) 4 (116 mg, 0.1 mmol) was quickly added, and the reaction solution was heated to 110 C and refluxed for 24 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, and the toluene solvent was distilled off with a rotary evaporator. It was then separated and purified with a chromatography column using petroleum ether / dichloromethane as the eluent (volume ratio of 3: 2) to obtain Compound 2 (2.85 g, 81.2%) as a brown solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 18013-97-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Science and Technology; Yu Jiangsheng; Tang Weihua; Zhang Zhuohan; Liu Xin; Zhou Jie; Geng Renyong; Yang Linqiang; (25 pag.)CN110606856; (2019); A;,
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18013-97-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, This compound has unique chemical properties. The synthetic route is as follows.

Compound A under nitrogen stream in 500 ml flask add (4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b: 4,5-b’]dithiophene, 15 g, 0.0259 mol) and add tetrahydrofuran(THF) was dissolved in 100 ml and slowly added 10.6 ml of n-BuLi (2.5M in hexane) at 0C ,It stirred at 50C for 1 hour 30 minutes. After stirring, the solution was cooled to -78C., and the dried ZnCl 2 solution was slowly added to the reaction solution and diethyl 2,5-bromotetraphthalate(diethyl 2,5-dibromoterephthalate, 3.93 g, 0.010364 mol) was added thereto, and the mixture was refluxed and stirred for 12 hours. After completion of the reaction and extracted with water and dichloromethane (MC),Dry the organic layer with MgSO4 and perform column chromatography(hexane: MC = 2: 1)Compound B (11.9 g, 84%) was obtained.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Gyeongsang National University Industry-Academic Cooperation Foundation; Kwon Sun-gi; Kim Yun-hui; Kim Myeong-jong; (22 pag.)KR2019/64410; (2019); A;,
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Ester – an overview | ScienceDirect Topics

A common compound: 764667-64-3, name is 5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 764667-64-3

2,4,5-Trifluorophenylacetic acid (2-1) (150 g, 0.789 mol), Meldrum’s acid (125 g, 0.868 mol), and 4- (dimethylamino)pyridine (7.7 g, 0063 mol) were charged into a 5 L three-neck flask. N,N-Dimethylacetamide (DMAc) (525 mL) was added in one portion at room temperature to dissolve the solids. N,N-diisopropylethylamine (282 mL, 1.62 mol) was added in one portion at room temperature while maintaining the temperature below 40 C. Pivaloyl chloride (107 mL, 0.868 mol) was added dropwise over 1 to 2 h while maintaining the temperature between 0 and 5 C. The reaction mixture was aged at 5 C for 1 h. Triazole hydrochloride 1-4 (180 g, 0.789 mol) was added in one portion at 40-50 C. The reaction solution was aged at 70 C for several h. 5% Aqueous sodium hydrogencarbonate solution (625 mL) was then added dropwise at 20 – 45 C. The batch was seeded and aged at 20 – 30 C for 1-2 h. Then an additional 525 mL of 5% aqueous sodium hydrogencarbonate solution was added dropwise over 2-3 h. After aging several h at room temperature, the slurry was cooled to 0 – 5 C and aged 1 h before filtering the solid. The wet cake was displacement-washed with 20% aqueous DMAc (300 mL), followed by an additional two batches of 20% aqueous DMAc (400 mL), and finally water (400 mL). The cake was suction-dried at room temperature.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 764667-64-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; SOLVIAS AG; WO2005/97733; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

581065-95-4, These common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In the glove box under an atmosphere of dry nitrogen, a 3000 mL, 4-necked flask was charged with bis-CBZ-Lysine (200.0 g, 483 mmol), EDC (139 g, 724 mmol), and 1500 mL of 2:1 tetrahydrofuran:tert-butyl methyl ether. The flask was fitted with an immersion well; the remaining joints were stoppered, and the flask was transferred to the fume hood where one of the stoppers was replaced with an addition funnel connected by a gas inlet adapter to a bleed of dry nitrogen. The flask was placed in a salted ice-water bath, fitted with an overhead stirring apparatus, and stirred until 0[deg.] C. was attained. In the glove box under a dry nitrogen atmosphere, amino-dPEG(R)4-TBE (163 g, 507 mmol) was dissolved in tetrahydrofuran (170 ml). The PN10221 was then poured into the addition funnel under a nitrogen shower and added slowly by drop, keeping the temperature as close to [deg.] C. as possible. The reaction was allowed to continue overnight, warming slowly to ambient. The reaction appeared complete the next morning by TLC and RP-HPLC. Stirring of the reaction mixture was stopped, and the EDU was allowed to settle for several hours. The solution was then decanted from the EDU goo. The reaction solvent was removed by rotary evaporation under reduced pressure at 45[deg.] C. The residue was then dissolved in dichloromethane to a final volume of 1400 mL and washed once with 250 mL with 10% aqueous HCl, then once with 400 mL of 5% brine. The DCM was removed by rotary evaporation at 35[deg.] C., and the residue was dried by rotary evaporation at 45[deg.] C. under high vacuum for about 1 hour. Yield: 330 gms (95.4%) HPLC (AMINES3045FF METHOD): 96.2% purity by ELSD. TLC: Ethyl Acetate:Methanol 8:2. Major spot at Rf=0.69 with both UV quench at 254 nm and iodine-positive reaction. One minor UV quenching spot (no iodine reaction) near solvent front. No ninhydrin-positive spot. NMR: (400 MHz, CDCl3, [delta]): 7.322 (m, 11H, 2 CBZ rings & NH); 6.737 (s, 1H, amide); 5.762 (s, 1H, amide); 5.084 (m, 4H, 2*CH2O from CBZ); 4.153 (q, 1H, CHN on lysine); 3.526 (t, 2H, CH2 to N on lysine sidechain); 3.425 (t, 2H, CH2 [beta] to N on dPEG(R)); 3.164 (t, 2H, CH2N on PEG); 2.478 (t, 2H, CH2CO on PEG); 1.467 (m, 15H, lysine side chain alkyl methylene groups plus t-butyl ester). Quantitative NMR purity=96.8%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 581065-95-4.

Reference:
Patent; UNIVERSITY OF WASHINGTON; QUANTA BIODESIGN, LTD.; Davis, Paul D.; Wilbur, D. Scott; US2013/52130; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 82911-71-5, name is (9H-Fluoren-9-yl)methyl 1H-benzo[d][1,2,3]triazol-1-yl carbonate, A new synthetic method of this compound is introduced below., 82911-71-5

4-[Bis(tert-butyl)phosphonomethyl]-N-Fmoc-DL-phenylalanine (Compound No. 4) A solution of amine compound No. 3 (770 mg, 1.93 mmol) in dioxane (10 mL) is stirred at room temperature 20 min) with aqueous 1 N NaOH (10 mL, 10 mmol, 5 equiv.). Carbon dioxide is then bubbled in (resulting pH 8.0-8.5) and Fmoc-OBT (857 mg. 2.40 mmol, 1.2 equiv) is added as a suspension in dioxane (3*10 mL) and stirred overnight at ambient temperature. The reaction mixture is partitioned between cold aqueous 5% citric acid (200 mL) and CHCl3 (3*100 mL); the combined organic is washed with cold 5% citric acid (1*100 mL); brine (1*200 mL); dried (MgSO4) and taken to dryness, yielding a light yellow resin (1.92g). The resin is taken up in CHCl3 and filtered through a silica pad. Unreacted Fmoc-OBT and faster impurities are removed with CHCl3 (5*100 mL) with product then being eluted (8*100 mL) with 1% EtOH in CHCl3 and taken to dryness, providing a foam (953 mg) which is dissolved in Et2 O (5 mL) and cooled with petroleum ether (20 mL) to yield compound No. 4 as a white powder: 835 mg (73%); mp 65-70 C. (gas, dec.).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; The United States of America as represented by the Secretary of the Department of Health and Human Services; US5264607; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

581065-95-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, A new synthetic method of this compound is introduced below.

00332] tert- butyl (2-(2,6-dioxopiperidin-3-yl)-l,3-dioxoisoindolin-4-yl)glycinate (0. lg, (0733) 0.25mmol) was dissolved in lmL TFA. The mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure to afford solid product which was used in the following reaction without further purification. (2-(2,6-dioxopiperidin~3~yl)-i ,3- dioxoisoindoim-4-yl)giycme product (0.05g, 0.15mmol) was mixed with HATU (0. i l4g, 0.3mrnol) in 3mL DMF. EtsN (0.105mL, 0.75mmol) was added. The mixture was stirred for lOmins before the amino-PEG4-/~Butyl ester (0.05g, 0.15mmo) was added. The reaction was then stirred at room temperature overnight. The solution was next subjected to preparative HPLC purification to afford 48mg product (51%). LCMS (ESI) m/z 579.32 (0734) (show as free acid instead of /-butyl ester) [(M+H)+; calcd for CsoHisNiOiC; 635.29]

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUHRLAGE, Sara; ANDERSON, Kenneth C.; HIDESHIMA, Teru; GRAY, Nathanael S.; LIU, Xiaoxi; (137 pag.)WO2019/118728; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

581065-95-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 581065-95-4 name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

BOP (0.3 g, 0.73 mmol) and DIPEA (0.26 mL, 1.52 mmol) were added to a suspension of 11 (0.1 g, 0.15 mmol) and amino-CH2CH2-POE4-CO2tBu (0.21 g, 0.67 mmol) in DMF (6 mL). The reaction mixture was stirred for 96 hours at room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2, washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by size exclusion chromatography (Sephadex, LH20. GE Healthcare, CH2Cl2/MeOH 50/50) to give compound 12 (88%) in the form of a yellow oil. (0287) 1H NMR (300 MHz, CDCl3) delta (ppm) 1.45 (s, 36H, 4 tBu), 2.24 (bs., 1H, H alkyne), 2.30-3.00 (m, 24H, 4 CH2COOtBu, 6 CH2CONH PAMAM, 2 CONHCH2CH2NHCO), 3.10-3.71 (m, 88H, CH2N and NCH2 PAMAM, CH2O, 4 CONHCH2CH2O), 3.79 (m, 2H, CH2 alkyne), 5.30 (m, 2H, NH), 7.20 (m, 4H, NH); 13C NMR (75 MHz, CDCl1) delta (ppm) 173.2, 170.9, 170.7, 80.3, 73.9, 70.4, 70.3, 70.2, 70.0, 69.9, 69.2, 52.7, 50.5, 49.0, 39.9, 39.1, 36.0, 33.1, 27.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE STRASBOURG; UNIVERSITE CLAUDE BERNARD LYON 1; HOSPICES CIVILS DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE -CNRS; FELDER-FLESCH, Delphine; BILLOTEY, Claire; PARAT, Audrey; GAROFALO, Antonio; KRYZA, David; JANIER, Marc; (138 pag.)US2016/221992; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics