Month: September 2021

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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

The 2-methyl-3-amino-5-bromobenzoic acid methyl ester (1.5g, 6 . 1mmol) dissolved in 15 ml chloroform, by adding potassium acetate (0.63g, 6 . 4mmol) and acetic anhydride (1.26g, 12 . 3mmol), stirring the mixture at room temperature for 12 hours. Then added tert-butyl nitrite (2.53g, 24 . 6mmol) and 18-crown -6 (0.57g, 2 . 15mmol), 65 C lower stirring 3 hours. After finishing the reaction, cooling to room temperature, add saturated sodium bicarbonate aqueous solution and dichloromethane, separating, sodium sulfate drying, extraction, concentration to obtain the product.

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; Sichuan Univeristy; Yu, Luoting; Wei, Yuquan; (54 pag.)CN105037360; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, 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 35418-07-6, Computed Properties of C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white 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, Methyl 3-(4-aminophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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Application of 148547-19-7, 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. 148547-19-7 name is Methyl 4-bromo-3-methylbenzoate, 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.

Step A. (2-Methyl-2′-methoxy-[1,1′-biphenyl]-4-yl)carboxylic acid methyl ester A mixture of 3-methyl-4-bromobenzoic acid methyl ester (2.0 g, 8.7 mmol), 2-methoxyphenyl boronic acid (1.32 g, 8.7 mmol) and sodium carbonate (4.1 g, 38.7 mmol) in toluene:ethanol:water (50 mL:25 mL: 25 mL) was purged with nitrogen for 1 hour. After addition of the tetrakis(triphenylphosphine) palladium(0) catalyst (0.50 g, 0.43 mmol), the reaction mixture was heated at 100 C. overnight. After cooling, the reaction was filtered through Celite and the cake washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown oil. Purification by flash chromatography on silica gel with a solvent gradient from 20% to 50% dichloromethane in hexane gave 2.0 g of product as a colorless oil. 1H NMR (DMSO-d6, 400 MHz): delta2.09 (s, 3H), 3.70 (s, 3H), 3.85 (s, 3H), 7.00-7.04 (m, 1H), 7.08-7.11 (m, 2H), 7.23 (d, 1H), 7.37-7.41 (m, 1H), 7.77-7.79 (m, 1H), 7.83-7.84 (m, 1H). MS [(+)APCI, m/z]: 257[M+H]+. Anal. Calcd. for C16H16O3: C, 74.98, H, 6.29. Found: C, 74.06, H, 6.17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2003/8863; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2672-58-4, 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. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 1,3,5-Tris(hydroxymethyl)benzene A solution of trimethyl 1,3,5-benzenetricarboxylate (8.83 g, 0.035 M; Aldrich) in THF (125 mL) is added dropwise over a period of 45 minutes to a stirred mixture of lithium aluminum hydride (3.98 g, 0.105 M) and dry THF (150 mL) under a nitrogen atmosphere. The initial phase of the addition results in vigorous reaction and consequently the addition is very slow at first. As the ester solution is added, an orange mass forms when the drops came in contact with the LiAlH4 mixture. A yellowish-green mixture results and is stirred at room temperature. The excess LiAlH4 is quenched carefully by the addition of ethyl acetate and the resulting mixture is acidified with aqueous 2N HCl solution until the pH is <3 and aluminum salts have dissolved. The layers are separated and the aqueous layer is extracted 3 times with additional ethyl acetate and then with methylene chloride. The organic extract layers are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give a white solid (2.98 g, 51%). Recrystallization from acetonitrile-methylene chloride gives the title compound as white crystals (1.13 g) which appear to be hygroscopic when collected by suction filtration. The crystals are dried several days over P2 O5 in a vacuum desiccator after which they have amp of 76.5-78 C. 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, Trimethyl benzene-1,3,5-tricarboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; The Upjohn Company; US5500417; (1996); A;,
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Some common heterocyclic compound, 142166-01-6, name is Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate, molecular formula is C10H11NO3, 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. SDS of cas: 142166-01-6

Step 3: 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (1 g, 5.2 mmol) was dissolved in MeOH (5 ml) and THF (10 ml) in a 25 mL flask, to which LiOH (2 g) dissolved in H2O (5 ml) was added, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, the solvent was concentrated. The pH of the reaction mixture was adjusted to 5 by using 2N HCl. The mixture was extracted with EA. The organic layer was dried over MgSO4 and filtered. As a result, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid was obtained (1.2 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 142166-01-6, its application will become more common.

Reference:
Patent; Hyundai Pharm Co., Ltd.; LEE, In Hee; CHAE, Hee Il; KIM, Se hoan; MOON, Soon Young; HA, Tae Young; CHOI, Hyo sun; KIM, Young Seok; KIM, Chun hwa; RHEE, Jae Keol; (132 pag.)US2016/355483; (2016); 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. 6279-86-3, name is Triethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H16O6

Example 2N-r(7-hvdroxy-5-oxo-4,5-dihvdropyrazolori,5-alpyrimidin-6-yl)carbonyllglvcine A mixture of lH-pyrazol-5-amine (0.20 g, 2.40 mmol), triethyl methanetricarboxylate (0.51 mL, 2.40 mmol), glycine (0.27 g, 3.60 mmol) and l,8-diazabicyclo[5.4.0]undec-7-ene (0.68 mL, 4.80 mmol) in ethanol (5.0 mL) was heated to 180 0C for 20 minutes in a Biotage Initiator microwave synthesizer. The mixture was purified via preparative HPLC (YMC 75 X 30 mm column, 0.1% TFA in water and 0.1% TFA in acetonitrile) to afford the title compound as a yellow solid (0.065 g, 11%). 1H NMR (400 MHz, OMSO-d6) delta ppm 13.0 (s, 2 H) 9.87 (t, J=5.6 Hz, 1 H) 7.85 (d, J=2.0 Hz, 1 H) 6.01 (d, J=LO Hz, 1 H) 4.16 (d, J=5.8 Hz, 2 H). MS(ES+) m/e 253 [M+H]+.

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; SMITHKLINE BEECHAM CORPORATION; WO2009/39323; (2009); 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. 106-32-1, name is Ethyl octanoate, A new synthetic method of this compound is introduced below., Formula: C10H20O2

General procedure: In a typical run, a 50 mL stainless steel autoclave equipped with a transducer for online pressure monitoring was charged under air of Pd-pol (10.6 mg, Pd: 0.5 mol%), the substrate (carboxylic acid or ester, 1.0 mmol), bromobenzene (0.1 mmol, 15.7 mg) and alcohol (5.0 mL). The autoclave was then purged three times with hydrogen, then pressurized with 2 bars H2, set on a magnetic stirrer and heated to 40 C. After the minimum time needed to reach reaction completion, the autoclave was let to reach room temperature, the hydrogen was vented and the autoclave opened. When necessary, 3.0 mL diethyl ether was added to the mixture at the end of reaction in order to dissolve organic reactants and products. The catalyst was recovered by centrifugation. The yields were assessed by GLC analysis of the organic solution by using biphenyl (50.0 mg) as internal standard.

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:
Article; Dell’Anna, Maria Michela; Capodiferro, Vito Filippo; Mali, Matilda; Mastrorilli, Piero; Journal of Organometallic Chemistry; vol. 818; (2016); p. 106 – 114;,
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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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Product Details of 5445-17-0

The 2.50g (9.05mmol) of tert-butyl 2 – [(benzylamino) methyl] azetidine-1-carboxylate [racemate] was dissolved in dichloromethane (150ml), the 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromo-propionate [racemate] was added and the mixture was stirred overnight at room temperature. Was added 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromopropionate [racemate], and the mixture was stirred overnight at 40 . Then additional 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromopropionate [racemate], and the mixture was at 40 overnight with stirring. After cooling to room temperature, the mixture was diluted with dichloromethane and washed with water, and the phases were separated. The aqueous phase was extracted twice with dichloromethane and the combined organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and then the solvent was removed under reduced pressure. The crude product obtained was purified as follows: silica gel chromatography (dichloromethane, then dichloromethane / methanol = 100: 1). Yield: 3.22g (94%, based on the theoretical value).

The synthetic route of 5445-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Allerheiligen, S.; Buchmuller, A.; Engel, K.; Gerdes, C.; Gericke, K. M.; Gerisch, M.; Heitmeier, S.; Hillisch, A.; Kinzel, T.; Lienau, P.; Riedl, B.; Rohrig, S.; Schmidt, M. V.; Strassburger, J.; Tersteegen, A.; (223 pag.)CN105408331; (2016); 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. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H11NO3

To a solution of compound 1 (50 g, 276 mmol) in CHCb (600 mL) was added SO2CI2 (26 mL, 331 mmol) in an ice bath and stirred at reflux for 4 hours. The reaction mixture was concentrated to afford the crude product, which was purified by trituration with PE/EA = 1 : 1 (200 mL) to get desired product as white solid (36 g, 61% yield). 1H MR (400 MHz, DMSO-d6) delta: 7.64 (IH, s), 6.48 (IH, s), 3.81 (3H, s), 3.75 (3H, 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 50413-30-4.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 4934-99-0 as follows. category: esters-buliding-blocks

Step 1: methyl 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yI)cyclobutane-l- carboxylate: into a 1000-mL round-bottom flask, was placed a solution of methyl 3- hydroxycyclobutane-l -carboxylate (10 g, 76.88 mmol, 1.00 eq.) in tetrahydrofuran (500 mL), 2,3-dihydro-l H-isoindole-l,3-dione (13.2 g, 89.7 mmol, 1.20 eq.), triphenyl phosphine (23.6 g, 90.0 mmol, 1.20 eq.). This was followed by the addition of DEAD (21 g, 120.6 mmol, 1.50 eq.) dropwise with stirring. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1). This resulted in 6 g (30%) of methyl 3-(l ,3-dioxo-2,3- dihydro-l H-isoindol-2-yl)cyclobutane-l -carboxylate as a white solid. NMR (300MHz, CDC ): delta 7.85-7.81 (m, 2H), 7.75-7.70 (m, 2H), 5.09-5.03 (t, J= 8.7 Hz, 1 H), 3.32-3.29 (m, 1 H), 3.18-3.10 (m, 2H), 2.67-2.59 (m, 2H), 1.31 -1.24 (m, 3H). LC-MS: (M+H)+ = 260.

According to the analysis of related databases, 4934-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (96 pag.)WO2016/105468; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics