Month: July 2021

Application of 927-68-4, 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 927-68-4 as follows.

EXAMPLE 128a Preparation of intermediate Acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester To a solution of 2-hydroxy-5-methyl-benzaldehyde (2.4 g, 18 mmol) (Aldrich) in N,N-dimethylformamide (30 mL) was added cesium carbonate (6 g, 18 mmo), potassium iodide (3 g, 18 mmol) and 2-bromoethyl acetate (7 g, 42 mmol), Aldrich). The reaction mixture was heated at 100 C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl ether, washed with water, brine, separated, and concentrated. The residue was purified by chromatography (EtOAc:Hexanes=1:6) to give acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester as a yellow oil (Yield 4 g, 100%).

According to the analysis of related databases, 927-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chen, Li; Ding, Qingjie; Liu, Jin-Jun; Yang, Song; Zhang, Zhuming; US2007/213341; (2007); A1;,
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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. 1139-13-5, name is Diethyl cyclohexane-1,1-dicarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C12H20O4

Example 9 Preparation of 1-fluoromethylcvclohexylalanine P2 building block Cyclohexane-1,1-dicarboxylic acid diethyl ester,1 , was prepared in accordance with JACS 43, 1921, 1368 from diethyl malonate and 1 ,5-dibromopentane.Cyclohexane-1,1-dicarboxylic acid diethyl ester, 1 , was taken up in anhydrous THF under nitrogen at room temperature. This was treated with LiAI(O1Bu)3H (2.5eq) portionwise before refluxing overnight. The reaction mixture was cooled in an ice-bath and treated carefully with 10% KHSO4(aq) and allowed to stir for 10 minutes. The resulting precipitate was removed by vacuum filtration and the mother liquors were partitioned between EtOAc and brine. The organic phases were combined, dried over MgS04, filtered and concentrated in vacuo to give a mobile oil. This was purified by flash column chromatography to give 1-hydroxymethyl- cyclohexanecarboxylic acid ethyl ester, 2 as a colourless oil (51%). EPO 1-Hydroxymethyl-cyclohexanecarboxylic acid ethyl ester, 2 was taken up in [bis (2- methoxyethyl) amino] sulphur trifluoride and heated overnight at 7O0C. The reaction was then allowed to cool to O0C and carefully treated with saturated NaHCO3 (aq) dropwise. This was stirred at room temperature for 30 minutes. The mixture was washed twice with DCM and the combined organics were washed with saturated NaHCO3 (aq) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give 1 -fluoromethyl-cyclohexane carboxylic acid ethyl ester, 3, as a colourless oil (34%)1-Fluoromethyl-cyclohexane carboxylic acid ethyl ester, 3, was dissolved in anhydrous THF and cooled under a nitrogen atmosphere to O0C. This was treated portionwise with LiAIH4 (2eq) and warmed to room temperature for 4 hours. After this time the reaction was cooled to O0C and carefully treated with 2M HCI(aq) and stirred for 20 minutes. The reaction was filtered through a pad of celite and the pad was washed with diethyl ether. The collected solution was partitioned between brine and diethyl ether. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo to give an oil. This was purified by flash chromatography to give (1- fluoromethyl-cyclohexyl) methanol, 4, as a colourless oil (67%).(1 -Fluoromethyl-cyclohexyl) methanol, 4, was dissolved in anhydrous DCM under N2 and cooled to -2O0C. NEt3 (1.1eq) was added and the reaction was stirred for 5 minutes. This was then treated dropwise with triflic anhydride (1 1eq) and the solution was stirred at O0C for 1hour. The reaction mixture was poured onto ice and the organics were washed with 1M HCI (aq), saturated NaHCO3 (aq) and brine, then dried over MgSO4, filtered and concentrated in vacuo, to give trifluoro-methanesulfonic acid-1-fluoromethyl-cyclohexylmethyl ester, 5, as an amber oil which was used immediately without further purification in the next step.N-(Diphenylmethylene)glycine ethyl ester was dissolved in DMF and under a nitrogen atmosphere was cooled to O0C. This was treated with KO’Bu (1.1eq) and stirred for 20 minutes. To this solution was added trifluoro-methanesulfonic acid-1-fluoromethyl-cyclohexylmethyl ester, 5 dropwise. The reaction mixture was stirred at room temperature under nitrogen overnight then poured into a 1 :1 mixture of diethyl ether : NH4CI (aq). The phases were separated and the aqueous phase was washed twice with diethyl ether. The organic phases were combined and washed several times with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give 2-(benzhydrylidene- amino)-3-(1 fluoromethyl-cyclohexyl) propionic acid ethyl ester, 6 (28%).2- (Benzhydrylidene-amino)-3-(1-fluoromethyl-cyclohexyl)propionic acid ethyl ester, 6, was taken up in 1,4-dioxan and treated with 2 M NaOH (aq) (2eq) with stirring. After the starting EPO material had been consumed (tic), the reaction mixture was acidified by addition of 2M HCI (aq) and stirred overnight at room temperature. The solution was concentrated in vacuo and the residue was partitioned between TBME and water. The pH of the aqueous phase was adjusted to p H 7 by careful addition of 2M NaOH (aq) prior to lyophilisation. The resulting residue was then suspended in 10% Na2CO3 (aq) and dioxan until a homogeneous solution was obtained. Fmoc chloride was added portion wise to the ice-cooled solution over 12 hrs and this was allowed to stir at room temperature overnight. The reaction mixture was washed with TBME and the resulting aqueous was acidified with 2M HCI (aq) and allowed to freeze dry. The resulting solid was triturated with methanol and the mother liquors were collected by filtration and concentrated in vacuo. To remove last traces of salts the resulting solids were partitioned between water and ethyl acetate. The organics were dried over MgSO4, filtered and concentrated in vacuo to give 2-(9H-fluoren-9-ylmethoxycarbonylamino)-…

The synthetic route of 1139-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR UK Ltd; PEPTIMMUNE, Inc; WO2006/64286; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 63485-50-7, 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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Triphenylphosphine (830 mg, 3.16 mmol) was added to a solution of 4-fluoro-2- methoxyphenol (0.300 mL, 2.63 mmol) in tetrahydrofuran (2 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (0.34 mL, 3.2 mmol) was added, followed by DIAD (0.61 mL, 3.2 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 12 h and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-50% EtOAc-hexanes gradient to give the title compound (666 mg, 100%). 1H NMR (400 MHz, CD3SOCD3) delta 2.24-2.40 (m, 2 H), 2.58 (ddd, J = 13, 7, 4 Hz, 2 H), 3.09-3.18 (m, 1 H), 3.62 (s, 3 H), 3.72 (s, 3 H), 4.71 (t, J = 7 Hz, 1 H), 6.56-6.66 (m, 1 H), 6.67-6.77 (m, 1 H), 6.88 (d, J = 3 Hz, 1 H); LC-MS (LC-ES) M+H = 255.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 139102-34-4, 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 139102-34-4 as follows.

Example 25A methyl 4-(4-((4′-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)-2-methoxybenzoate Methyl 4-bromo-2-methoxybenzoate (700 mg), EXAMPLE 7B (983 mg), K3PO4 (909 mg), tris(dibenzylideneacetone)dipalladium(0) (78 mg), and 2-(di-t-butylphosphino)biphenyl (102 mg) were stirred in 1,2-dimethoxyethane (10 mL) at 80 C. for 24 hours. The reaction mixture was chromatographed on silica gel with 20-50% ethyl acetate/hexanes.

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); 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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., Computed Properties of C7H11ClO4

Example 15 Synthesis of ethyl 4-hydroxy-2-[2′-(trifluoromethyl)biphenyl-3-yl]-1,3-thiazole-5-carboxylate (15) 3-Bromobenzenecarbothioamide (1.00 g, 4.62 mmol) and diethyl chloropropanedioate (1.0 mL, 6.0 mmol) were dissolved in dioxane (35 mL). The mixture was heated at 80°C and stirred overnight, whereupon the solvent was removed under vacuum. Ethyl 2-(3-bromophenyl)-4-hydroxy-1,3-thiazole-5-carboxylate was obtained as a yellow solid (1.09 g, 72percent) by trituration in acetonitrile.

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; Dompe’ S.P.A.; Moriconi, Alessio; Bianchini, Gianluca; Colagioia, Sandro; Brandolini, Laura; Aramini, Andrea; Liberati, Chiara; Bovolenta, Silvia; EP2606888; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, 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 17205-02-6, Quality Control of Ethyl 3-hydroxycyclobutanecarboxylate

To a diethyl ether solution (30 mL) containing methyl magnesium bromide (7.63 mL of a 3.0 M diethyl ether solution) was added a diethyl ether solution (5 mL) containing ethyl 3- hydroxycyclobutane carboxylate (2.05 g, 6.94 mmol), dropwise. After two hours, the reaction was carefully quenched with 3 M aqueous hydrochloric acid. Magnesium sulfate was added until the evolution of gas stopped. The solution was filtered, and the solvent removed in vacuo yielding a viscous oil which was purified by silica gel chromatography, eluting with ethyl acetate:hexanes (1 :1 to 1 :0) to give 3-(2-hydroxypropan-2-yl)cyclobutanol (419 mg, 3.22 mmol, 46%). 1H NMR (CDCI3) delta 1 .13 (s, 6 H), 1 .74-1 .86 (m, 4 H), 2.23-2.39 (m, 2 H), 2.66 (br s, 1 H), 4.03-4.09 (m, 1 H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; SHEARER, Barry George; YOUNGMAN, Mark Andrew; (214 pag.)WO2018/229629; (2018); 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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 29823-21-0

Example 15Synthesis of Ethyl 8-nitrooxy-octanoate; 20.0 mmol Ethyl 8-bromooctanoate dissolved in 80 ml acetonitrile and 50.0 mmol silver nitrite were added into a flask protected from light. This suspension was stirred for 18 hours at 70 C. After cooling to room temperature the suspension was filtrated over silica gel, washed with Ethylacetate and concentrated in vacuo.The crude product was purified by flash chromatography on silica gel using heptane/ethyl acetate 4:1; Yield: 4.35 g (18.6 mmol, 93.2%).

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; Duval, Stephane; Kindermann, Maik; US2012/315339; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, 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. Product Details of 773873-95-3

Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0 C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0 C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 38 mmol, 76% over two steps) as a colorless oil.

The synthetic route of 773873-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; US2007/244159; (2007); 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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., Application In Synthesis of Diethyl fluoromalonate

Sodium metal (9.68 g, 421 mmol) was cut in small pieces and added to dry EtOH (300 mL) in portions. After all the sodium was dissolved, morpholine-4-carboxamidine sulfate (30 g, 168 mmol) and diethyl fluoromalonate (30 g, 168 mmol) were added to the mixture at 10 C. The resulting white suspension was stirred at 20 C. for 10 min and then heated under reflux for 12 h. The resulting purple suspension was concentrated under reduced pressure and water (150 mL) was added. The solution was treated with 6N HCl (60 mL) to obtain pH-4 at 10 C. The resulting yellow precipitate was collected by filtration, washed with water (40 mL*2) and the yellow filter cake was dried under an infrared lamp for 12 h to give 34 g (94%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 3.65-3.57 (m, 4H) 3.53-3.46 (m, 4H); m/z (APCI-) for C8H10FN3O3 214.1 (M-H)-.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; Chen, Ping; CHENG, Hengmiao; Gallego, Gary Michael; Jalaie, Mehran; Kath, John Charles; Orr, Suvi Tuula Marjukka; PAIRISH, Mason Alan; (100 pag.)US2017/15689; (2017); A1;,
Ester – Wikipedia,
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Synthetic Route of 4934-99-0, A common heterocyclic compound, 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, molecular formula is C6H10O3, 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.

At -10 , to 3-hydroxy-cyclobutane carboxylate (3.2g, 24.61mmol, 1eq.) In DCM (100mL) was added triethylamine(10.25mL, 73.83mmol, 3eq.) And methanesulfonyl chloride (2.29mL, 29.54mmol, 1.2eq.), The reaction was stirred at -10 3h. again60mL saturated ammonium chloride solution was added, the separated organic phase was washed with saturated sodium chloride solution (50mL x 2), dried over anhydrous sodium sulfate, and thenAfter concentration under reduced pressure, the residue was concentrated by silica gel column chromatography (eluent: PE / EtOAc (V / V) = 5/1) to give the title compound as a colorless oil (4.9 g of,95.7%).

The synthetic route of 4934-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd. of Guangdong; Ren, Qingyun; Luo, Huichao; Tang, Changhua; Zhang, Jiancun; Zhang, Yingjun; (30 pag.)CN104447583; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics