Month: September 2021

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 59833-69-1 as follows. 59833-69-1

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
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Related Products of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRADSHAW, Curt W.; Sakamuri, Sukumar; Fu, Yanwen; Oates, Bryan; Desharnais, Joel; Tumelty, David; US2009/98130; (2009); A1;,
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Some common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, molecular formula is C10H17NO2, 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. HPLC of Formula: C10H17NO2

At RT, 258 mg (1.41 mmol) of methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 402 mg (1.06 mmol) of HATU and 182 mg (1.41 mmol) of DIPEA were added to a solution of 210 mg (0.71 mmol) of 6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid in 5 ml of DMF. The mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was filtered off, washed with water and dried under reduced to pressure. This gave 326 mg (97% of theory, purity 98%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 8.05 (d, 1H), 7.77 (dd, 1H), 7.66 (d, 1H), 7.60-7.47 (m, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.09-2.00 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=463 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 135908-33-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEININGHAUS, Mark; TERJUNG, Carsten; MUENSTER, Uwe; OLENIK, Britta; (92 pag.)US2018/36300; (2018); A1;,
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555-43-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 555-43-1, name is Propane-1,2,3-triyl tristearate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Into a single-necked reaction flask, 1 equivalent of myristin (0.27 g, 0.37 mmol) and 3 equivalents of 11-(hexadecylthio)undecan-1-ol (0.48 g, 1.12 mmol) were added. After the addition of the catalyst (0.030 g, 15 mmol%), the mixture was heated with stirring in glycerin bath at 110 C (bath temperature) for 6 h, at the end of which the reaction mixture was cooled and sufficient amount of MeOH was added. The resulting solid product was filtered under vacuum and washed successfully with MeOH. The yield of 11-(hexadecylthio)undecyl tetradecanoate was 0.67 g, 93%. The productis of sufficient purity for further spectroscopic analysis.

The synthetic route of Propane-1,2,3-triyl tristearate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Y?ld?r?m, Ayhan; K?raylar, Kaan; Oeztuerk, Serkan; Research on Chemical Intermediates; vol. 46; 1; (2020); p. 215 – 230;,
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Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Part A: 5-Fluoro-4,6-dihydroxy-2-methylpyrimidine A solution of 200 ml. of 25% wt sodium methoxide in methanol (0.84 mol) was diluted with an additional 200 ml. of methanol. Acetamidine-HCI (40 g , 0.42 mol) was added to the sodium methoxide solution (white precipitate formed), followed by addition of dimethyl fluoromalonate (70 g, 0.46 mol). The contents were stirred at room temperature overnight, then concentrated in vacuo to dryness. The resulting residue was redissolved in hot water (300 ml_). After cooling the aqueous solution to room temperature, concentrated HCI was added slowly until crystal formation (fine white prisms) took place at about pH 5. Concentrated HCI was added dropwise until pH 3, and then the contents were filtered. The isolated crystals were rinsed with 1 M HCI and dried under vacuum to provide 5-fluoro-4,6-dihydroxy-2-methylpyrimidine (65.5 g, >100%). LCMS: (M+H)+: 145.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
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Application of 1731-79-9, These common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, 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.

To a cooled (0 C) solution of LiAlH4 (1.73 g, 45.6 mmol) in THF (280 mL) was added a solution ofdimethyl dodecanedioate (4.35 g, 15.2 mmol) in THF (20 mL) dropwise, and the resulting solution wasstirred at 0 C for 3 h. Then, the reaction mixture was quenched with MeOH and 1 M HCl. The organic layer wasseparated and the aqueous layer was extracted with diethyl ether three times. The combined organic layer was washedwith water and brine, and dried over sodium sulfate. After evaporation of the solvent, the product was obtained(3.22 g, 92%) in high purity, which was then used in the next step without further purification.1H-NMR (500 MHz, CDCl3): delta3.64 (t, J =7.5 Hz, 4H, 1-H, 14-H), 1.57 (m, 4H, 2-H, 13-H), 1.35-1.26(20H, 3-H to 12-H)13C-NMR (125 MHz, CDCl3): delta63.1 (C1, C14), 32.8 (C2, C13), 29.6, 29.6, 29.5, 29.4 (C4 to C11), 25.7(C3, C12)HR-MS (ESI-TOF): m/z calcd for C14H30O2Na [M+Na]+ 253.2138, found 253.2137IR (film): 3409, 3347, 2923, 2854 cm

The synthetic route of 1731-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tonoi, Takayuki; Kawahara, Ryo; Yoshinaga, Yutaka; Inohana, Takehiko; Fujimori, Keiko; Shiina, Isamu; Tetrahedron Letters; vol. 56; 11; (2015); p. 1356 – 1359;,
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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. 541-16-2, name is Di-tert-Butyl malonate, A new synthetic method of this compound is introduced below., Computed Properties of C11H20O4

7a. Preparation of (1R,2R)/(1S2S) 1-amino-2-ethylcyclopropanecarboxylic Acid tert-butyl Ester (Racemic Mixture); Step 1: Preparation of 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester, Shown Below To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred for 18 hours at room temperature and treated with a mixture of ice and water. The crude product was extracted with dichloromethane (3*) and sequentially washed with water (3*), and brine. The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography (100 g SiO2, 3% diethyl ether in hexane) to provide the desired product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 426-65-3, name is Ethyl Pentafluoropropionate, 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. 426-65-3

General procedure: Sodium hydride (4.0 g, 100 mmol, 60% dispersion in mineral oil) was placed in a 500mL round-bottom flack and 50 mL of dry hexane was added. The suspension was stirred for a short time with a magnetic stirring bar and kept until the hexane layer became clear (20-30 min). Hexane was cautiously removed with a glass pipette until a wet paste of NaH remained. This procedure was repeated twice. After that, THF (150mL) was added with vigorous stirring. Anhydrous EtOH (0.5 mL) was added in oneportion at 0 C, followed by the dropwise addition of a solution of 2-acetylthiophene (6.3g, 50 mmol, 5.42 mL) and methyl or ethyl ester of the respective perfluorinatedcarboxylic acid (50.5 mmol) in 30 mL of THF. The white suspension rapidly turns pink and then reddish-brown. Caution Hydrogen evolved during the addition and notable effervescence was observed. The rate of addition was maintained to control the evolution of hydrogen; usually the addition takes 60-80 min. When gas evolution ceased, the cooling bath was removed and the reaction mixture was stirred for 5 h. After that, the dark brown solution with a small amount of precipitate was re-cooled to 0 C,10 mL of anhydrous EtOH was added slowly to decompose traces of NaH, and the resulting solution was stirred for 30 min. The solvent was removed by evaporation under reduced pressure (100 Torr, bath temperature 40 C), then EtOAc (40 mL) andsubsequently a mixture of conc. HCl (20 mL) and crushed ice (80 mL) were added tothe residue. The resulting turbid liquid was shaken by hand until two clear layers formed. The organic phase was separated and the aqueous phase was then extracted with EtOAc (3 × 50 mL). The combined organic fractions were washed with brine (50mL), dried over MgSO4 and evaporated to dryness. The resulting brown oil was distilled in vacuo (2-3 Torr). The main fraction is pure enough. Additional portions of pure diketone can be separated from low-boiling fractions by precipitation as a copper salt. Decomposition should be performed with HCl (procedure A).

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 426-65-3.

Reference:
Article; Taydakov, Ilya V.; Kreshchenova, Yuliya M.; Dolotova, Ekaterina P.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 3106 – 3111;,
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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 51760-21-5 as follows. COA of Formula: C10H9BrO4

Step b) 5-(5-Methyl-l,l-dioxo-llambda*6*-ri,2,51thiadiazolidin-2-yl)-isophthalic acid dimethyl ester (Acid- 12b^; Tris(dibenzylideneacetone)palladium (27 mg, 0.029 mmol) was added to a degassed mixture of 5-bromo-isophthalic acid dimethyl ester (159 mg, 0.583 mmol), 2-methyl-[l,2,5]thiadiazolidine 1,1 -dioxide (Acid- 12a) (79 mg, 0.583 mmol), Cs2CO3 (474 mg, 1.46 mmol) and Xantphos (50.6 mg, 0.0874 mmol) in dioxane (5 ml). The mixture was heated at 105 0C under N2 for 2 h, the solvent was evaporated and the residue purified by flash chromatography using 2% MeOH in DCM as eluent, which gave the title compound (143 mg, 75%) as a yellow solid.

According to the analysis of related databases, 51760-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIVIR AB; LUNDBERG, Stina; AYESA, Susana; BELDA, Oscar; DORANGE, Ismet; ERSMARK, Karolina; HAMMER, Kristin; JOHANSSON, Per-Ola; LINDSTROeM, Stefan; ROSENQUIST, Asa; SAMUELSSON, Bertil; BAeCK, Marcus; KVARNSTROeM, Ingemar; WANGSELL, Fredrik; BJOeRKLUND, Katarina; WO2010/42030; (2010); A1;,
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Electric Literature of 23426-63-3,Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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.

Step B; 2,5-Dimethyl-4-thiocyanato-phenol 82 (5.75 g, 32.1 mmol) is dissolved in acetonitrile (25 mL) . Powdered cesium carbonate (15.32 g, 47.0 mmol) is added. Then 2-bromo-2- methyl-propionic acid methyl ester (4.50 mL, 34.8 mmol) is added and the mixture is stirred at 600C for 18 h. Filtration and concentration, followed by silica gel chromatography (0- 50% ethyl acetate in hexanes) yielded 2- (2, 5-dimethyl-4- thiocyanato-phenoxy) -2-methyl-propionic acid methyl ester 83 as an oil: 1H-NMR (400 MHz, CDCl3) (rotamers are present; the data given is for the most abundant isomer) delta = 7.39 (s, IH), 6.50 (S, IH), 3.78 (s, 3H)7 2.42 (s, 3H), 2.20 (s, 3H), 1.62 (s, 6H). MS calcd. for C14H17NNaO3S (M+Na+) 302.1, found 302.1.

The synthetic route of 23426-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/56366; (2007); A2;,
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