Author: Jessica.F

2318-25-4, Name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 2318-25-4, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

.To a mixture of 281 g of Compound (I-4) suspended in 1.6 liters of acetonitrile, 210 ml of triethylamine was added while stirring at a room temperature. Following stirring for 30 minutes, 318 g of the foregoing Intermediate (I-3) and 36 ml of acetic acid were added in this order to react them. After reacting for 10 hours, 3 liters of water was added and stirring was continued. Precipitated crystals were collected by filtration. The crystals were washed with water and dried. As a result, 324 g (yield 71percent) of the objective Intermediate (I-5) was obtained, as a white crystal.

Statistics shows that Ethyl 3-ethoxy-3-iminopropionate hydrochloride is playing an increasingly important role. we look forward to future research findings about 2318-25-4.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US6649771; (2003); B2;,
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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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., 33993-24-7

EXAMPLE 37; Synthesis of cyclopropyl(2-isopropy]pyrazolo[l,5-a]pyridin-3-yl)methanone; 2-isopropyl-pyrazolo[l,5-a]pyridine (2.00 g, 12.4 mmol) was dissolved in cyclopropyl anhydride (8.00 g, 51.9 mmol). Concentrated H2SO4 (3 drops) was added at room temperature and the mixture was then heated to 140 0C for 28 hours. The mixture was then cooled to 0 0C, diluted with H2O (10 mL) and 50 % NaOH (aq) was added to achieve a solution pH of 11. This mixture was extracted with Et2O (3 x 10 mL). The combined organic layers were washed with H2O (15 mL), brine (15 mL), dried (Na2SO4), filtered and concentrated. The crude mixture was then immediately subjected to flash chromatography (90 % EtOAc/ hexane) to afford 1.02 g (4.4 mmol, 36 %) of the title compound as a white powder. This material was then recrystallized from n-heptane to afford 0.6115 g (2.7 mmol, 22 %) of SB-I1-61 was white needles, mp 72 0C (?-heptane); IR (thin film) v = 2969, 1635, 1506, 1439 1H NMR (300 MHz, CDCl3) delta = 8.42 (d, J= 6.8 Hz, IH), 8.09 (d, J= 9.0 Hz, IH), 7.33-7.27 (m, IH), 6.82 (ddd, J= 6.8, 6.8, 1.2 Hz, IH), 3.75 (sept, J = 6.9 Hz, IH), 2.47-2.39 (m, IH), 1.40 (d, J= 6.9 Hz, 6H), 1.27-1.17 (m, 2H), 0.99-0.93 (m, 2H); 13C NMR (150 MHz, CDCl3) delta = 194.8, 163.1, 141.6, 128.9, 127.4, 118.9, 113.2, 110.7, 27.8, 22.4, 20.4, 10.2; MS (EI) m/z 229 (M+ 1, 18.2), 228 (M+, 100.0), 213 (46.4), 200 (13.1), 199 (23.4), 198 (14.1), 185 (23.2), 171 (23.2), 160 (13.5), 145 (11.8), 132 (10.2), 131 (13.8), 119 (11.6), 117 (18.0), 92 (10.2 ), 91 (10.9), 90 11.0), 84 (11.2), 78 (17.6), 69 (24.6) 51 (10.9); HRMS (EI) calcd for C14H16N2O: 228.1263, found: 228.1261; Anal. Calcd for Ci4H16N2O: C, 73.66 %; H, 7.06 %; Found: C, 73.93 %; H, 7.25%. Compound 1046.

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; AVIGEN, INC.; WO2007/146087; (2007); A2;,
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61367-07-5, 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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

EDCI (19 mg, 0.097 mmol), HOBt (13 mg, 0.097 mmol), and DIEA (0.034 mL, 0.195 mmol) were added to a solution of carboxylic acid intermediate 13 (30 mg, 0.065 mmol) dissolved in DCM. After 10 minutes, methyl trans-4-aminocyclohexanecarboxylate hydrochloride (25 mg, 0.13 mmol) and a catalytic amount of DMAP were added. After stirring overnight, the solvent was removed and the crude product was purified by column chromatography to give the 30 mg of intermediate 18 as a white solid.

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; Sanofi; The Regents of the University of Michigan; US2012/289494; (2012); A1;,
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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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., 89-91-8

General procedure: To a solution of diisopropylamine (1.5 eq.) in THF (1.5M) at ooc under N2 was added nBuli(1.4eq., 1.6M in hexane) and the mixture was stirred for 20 min. The LOA was cooled to -80C20 and TMSCI (1.4 eq.) was added followed by the methyl ester (1 eq.). The reaction was allowedto reach ooc over 3 h, brought to rt and stirred for 30 min. Pentane was added and the whiteprecipitate filtered off over celite. The solvent was removed under reduced pressure. Purificationif necessary was performed by bulb-to-bulb distillation.

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; SANDOZ AG; HOEFERL-PRANTZ, Kathrin; FELZMANN, Wolfgang; WILHELM, Thorsten; BENITO-GARAGORRI, David; WO2013/189980; (2013); A1;,
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10601-80-6, 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (2.00 g, 50.6 mmol, 60%) was added to a solution of ethyl formate (10.13 g, 168.7 mmol) in tetrahydrofuran while maintaining the internal temperature below 0 C. Then, ethyl 3,3-diethoxy propionate (5.00 g, 33.75 mmol) was added dropwise to the reaction mixture and stirred for 24 h at ambient temperature. After confirming that the reaction was complete by using TLC analysis, the reaction was quenched with 20 mL water and the tetrahydrofuran was removed under reduced pressure. The mixture was extracted with ethyl acetate and then brine. The organic phase was dried over Na2SO4 overnight and the solvent was removed in vacuo to give the title compound 14.

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:
Article; Zhao, Shizhen; Zhang, Xiangqian; Wei, Peng; Su, Xin; Zhao, Liyu; Wu, Mengya; Hao, Chenzhou; Liu, Chunchi; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 96 – 107;,
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3196-15-4, name is Methyl 2-bromobutyrate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 3196-15-4

1.80 g (9.66 mmol) of tert-butyl 2-(aminomethyl)azetidine-1-carboxylate [racemate] were dissolved in 25 ml of dichloromethane, 1.62 ml (1.17 g, 11.6 mmol) of triethylamine and 1.11 ml (1.75 g, 9.66 mmol) of methyl 2-bromobutanoate [racemate] were added and the mixture was stirred under reflux overnight. 1.35 ml (0.98 g, 9.66 mmol) of triethylamine and 0.89 ml (1.40 g, 7.73 mmol) of methyl 2-bromobutanoate [racemate] were then added, and the mixture was stirred under reflux overnight. After cooling to room temperature, water was added and the phases were separated. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and then freed of the solvent under reduced pressure. This gave 2.64 g (83% of theory, purity: 87%) of the desired product. LC-MS (Method 6A): Rt=2.16 min (diastereomer 1, 2 isomers), Rt=2.22 min (diastereomer 2, 2 isomers); MS (ESIpos): m/z=287 [M+H]+

Statistics shows that 3196-15-4 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromobutyrate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ALLERHEILlGEN, Swen; BUCHMUeLLER, Anja; ENGEL, Karen; GERDES, Christoph; GERICKE, Kersten Matthias; GERISCH, Michael; HEITMEIER, Stefan; HILLlSCH, Alexander; KINZEL, Tom; LIENAU, Philip; RIEDL, Bernd; ROeHRIG, Susanne; SCHMIDT, Martina Victoria; STRASSBURGER, Julia; TERSTEEGEN, Adrian; (135 pag.)US2016/108027; (2016); A1;,
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34846-90-7, Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, belongs to esters-buliding-blocks compound, 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 34846-90-7.

Under nitrogen protection, add 12.9g (323.5mmol) of NaH and 150g of DMF to the reaction flask at -15-10¡ãC.4-amino-1,1,1-trifluoro-3-buten-2-one50 g (359.5 mmol) solution, the system turned from colorless to light yellow and finally to a red suspension,Methyl 3-methoxyacrylate (41.75 g, 359.5 mmol) was added dropwise and reacted at this temperature for 3 hours.Concentrated hydrochloric acid was added dropwise to the reaction flask at -10¡ãC to adjust the pH of 8-9. The system changed from a deep red suspension to orange, and water was added.1.5L of dilute hydrochloric acid was used to adjust the pH to 1 to 2, and a large amount of white flocculent solids precipitated. After stirring for 0.5 hours, 81.5 g of a white product was obtained by filtration (yield, 88.3percent).The NMR analysis of the product obtained in this example is shown in Figure 1.Prove that the resulting product isN-1-methoxy-2-methoxycarbonylethyl-4,4,4-trifluoro-3-keto-1-butenamine..

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, Methyl 3-methoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Heteng Fine Chemical Co., Ltd.; Chen Sheng; Shi Guancheng; Meng Haicheng; (8 pag.)CN107628991; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., 23877-12-5

Step 2: 1-[4-methylthiophenyl]-(E)-3-[3,5-dimethyl-4-tertiobutylcarbonyldimethylmethyloxyhenyl]prop-2-en-1-one (Intermediate 2) Caesium carbonate (87 g, 0.134 mol, 4 eq) and tetrabutylammonium iodide (12 g, 0.033 mol, 0.5 eq) are added to an intermediate solution 1 (20 g, 0.067 mol, 1 eq) in 50 ml of a DMSO/water mixture (3/2). The reaction medium is stirred for 30 minutes at 80 C. and tert-butyl bromoisobutyrate (30 g, 0.134 mol, 2 eq) is added. Then 2 additions of 2 eq of tert-butyl bromoisobutyrate diluted to 50% in DMSO are each made at an interval of 1 hour. The reaction medium is stirred for 2 days at 80 C. The reaction medium is left to cool to ambient temperature and then 1.5 litres of water are added and the product is extracted with dichloromethane (4 times). The organic phase is dried on a phase-separation cartridge and evaporated dry. Purification on silica gel (cyclohexane/ethylacetate: 95/5 to 80/20): 18 g (orange solid, yield: 61%).

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; NASHPHARM; LARUELLE, Claude; BONNAFOUS, Ludovic; US2020/23067; (2020); 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. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below., 344-14-9

Part A: 5-Fluoro-6-hydroxy-2-methylthio-4(1 H)-pyrimidinone To a stirred solution of 2-methyl-2-thiopseudourea sulfate (41.7 g, 0.15 mol) and dimethyl fluoromalonate (45 g, 0.30 mol) in MeOH (600 mL) at 0 C (ice bath) was added NaOMe (48.6 g, 0.90 mol) in portions. After the addition was complete, the ice bath was withdrawn and the reaction mixture was stirred at room temperature overnight. LCMS showed the formation of the desired pyrimidinone product. The reaction mixture was concentrated to near dryness under vacuum, diluted with water (50 mL), and acidified with 6N HCI (-150 mL) to ~pH 2 to precipitate the product. After filtration, the solid was washed with 1 N HCI (2 x 10 mL) and dried under vacuum to afford 5-fluoro-6- hydroxy-2-methylthio-4(1 H)-pyrimidinone (35.7 g, 68%) as a white solid. LCMS: (M+H)+: 177.3.

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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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. 110661-91-1 name is tert-Butyl 4-bromobutanoate, 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. 110661-91-1

Methyl 3-(4-(tert-butoxy)-4-oxobutoxy)beiizoate A solution of methyl 3Thydroxybenzoate (commercially available from for example Aldrich) (1 g, 6.6 mmol) and K2C03 (1.82 g, 13.2 mmol) in DMF (10 mL) was treated with tert-butyl 4-bromobutanoate (commercially available from for example Aldrich) (2.2 g, 9.9 mmol) and the mixture was stirred at 60 C for 16 hours. A further aliquot of K2C03 (1.82 g, 13.2 mmol) and tert-butyl 4-bromobutanoate (2.2 g, 9.9 mmol) were added and the mixture was heated at 60 C for further 6 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was washed with brine (2 x 50 mL), dried (hydrophobic frit) and evaporated to dryness. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (1.4 g, 4.8 mmol, 72 % yield). LCMS RT= 1.26 min, ES+ve m/z 312 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
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