Month: June 2021

Reference of 56741-34-5, 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. 56741-34-5 name is Methyl 5-amino-2-fluorobenzoate, 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: Methyl 5-{[(2,6-difluorophenyl)carbonyl]amino}-2-fluorobenzoate; To a solution of methyl 5-amino-2-fluorobenzoate (2.5 g, 14.8 mmol) (prepared according to literature precedence) in DCM (100 mL) at 0 0C, 2,6-difluorobenzoyl chloride (1.85 mL, 14.8 mmol) was added and the solution was allowed to stir for 30 min. The reaction mixture was quenched with H2O (50 mL). The organic layer was then washed with 1M NaOH (50 mL), dried over MgSO4, filtered and evaporated onto silica gel. The title compound of Step A was purified by chromatography, (25-100% EtOAc in hexanes). The title compound of Step A was obtained as a white solid in 69% yield (3.17 g). MS (ESI): 309.99 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/76140; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

In a dry argon-protected reaction tube, 4.0 mol% of [Pd(C3H5)Cl]2, 8.0 mol% was added successively.The mixture was stirred at room temperature for 30 minutes, then 1.0 equiv. 5 (0.2 mmol) was added and stirring was continued for 10 minutes. 3.0 equiv. 8 (1.5 mmol) and 3.0 equiv. of Base (1.5 mmol) were added to the reaction tube and the reaction was stirred. After the reaction is completed, the solvent is removed under reduced pressure and the residue is subjected to a thin layer chromatography to give the desired product (petroleum ether/dichloromethane = 1/1, or petroleum ether/ethyl acetate = 10/1, v/v).

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tongji University; Zhao Xiaoming; Gao Ning; Cai Chengsi; Cai Juewang; (20 pag.)CN104926720; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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 27492-84-8, Recommanded Product: Methyl 4-amino-2-methoxybenzoate

(a) Synthesis of methyl 4-(benzylamino)-2-methoxybenzoate Benzaldehyde (6.73 ml, 66.2 mmol) and acetic acid (3.77 ml, 66.2 mmol) were added to a solution of methyl 4-amino-2-methoxybenzoate (12 g, 66.2 mmol) in methanol (650 ml), and the resulting mixture was stirred at room temperature for 30 minutes. Then, acetic acid (7.56 ml, 132 mmol) and sodium cyanoborohydride (4.9 g, 79.4 mmol) were added thereto at 0°C and stirred at room temperature for 38 hours. The reaction mixture was concentrated, poured into a 1N-aqueous sodium hydroxide solution and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 2/1) to obtain methyl 4-(benzylamino)-2-methoxybenzoate (16.4 g, 91percent).

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 4-amino-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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 1. Synthesis of methyl 4-[(4-fluorobenzoyl)amino]-3-methylbenzoate Following standard procedure, 4-fluorobenzoic acid (0.510 g, 3.63 mmol), methyl 4-amino-3-methylbenzoate (0.500 g, 3.03 mmol), EDCI · HCl (1.16 g, 6.06 mmol), DMAP (0.930 g, 7.57 mmol) and CH2Cl2 (7.0 mL) were used to carry out the reaction. After the reaction mixture was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-40% ethyl acetate in n-hexane) to give methyl 4-[(4-fluorobenzoyl)amino]-3-methylbenzoate (0.380 g, 44%). 1H NMR (CDCl3, 400 MHz) delta 8.23 (d, 1H), 7.96-7.88 (m, 4H), 7.75 (br s, 1H), 7.20 (td, 2H), 3.91 (s, 3H), 2.39 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-methylbenzoate, its application will become more common.

Reference:
Patent; National Health Research Institutes; Ueng, Shau-Hua; Yeh, Shiu-Hwa; Lin, Shu-Yu; Shih, Chuan; (329 pag.)US2017/253569; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 41841-16-1, The chemical industry reduces the impact on the environment during synthesis 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, I believe this compound will play a more active role in future production and life.

Methyl 2-(4-bromophenyl)acetate (1.00 g, 4.37 mmol)Dissolved in anhydrous DMF (12.5mL),The reaction solution is under N2 protection,Add NaH (700 mg, 17.5 mmol, 60%) at 0 C.Stir for about 15 minutes,CH3I (1.62 mL) was added slowly.After the dropwise addition was completed, the reaction solution was further stirred at 0 C for 15 minutes.Then transfer to room temperature for 12 h.After the reaction with saturated ammonium chloride (20mL) The reaction was quenched and extracted with EA (20mL), the organic layer was washed with saturated brine (30 mL), thenAfter concentration under reduced pressure,To give the title compound as a yellow oily substance (1.12g, 99.8%).

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 2-(4-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ·geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
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. 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: 5-phenylpent-2-enoic acid (13) (0.18 g, 1.02 mmol) in DCM(2 ml) under argon atmosphere at rt was treated with a catalytic amount of DMF (1 drop) and oxalyl chloride (0.26 ml, 3.06 mmol). The mixture was stirred for 40 min and the volatiles were evaporated. The residue was dissolved in DCM (2 ml) and to the obtained solution at 0 C a mixture of ethyl 2-aminocyclohex-1-ene-1-carboxylate(0.26 g, 1.54 mmol) and triethylamine (0.14 ml,1.00 mmol) in DCM (1 ml) was added dropwise over 5 min. The mixture was stirred for 40 min at rt, then the mixture was supplemented with DCM, washed with saturated NH4Cl solution, brine,dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel (EtOAc in petroleum ether, 1:10 to1:6) to give crude ethyl (E)-2-(5-phenylpent-2-enamido)cyclohex-1-ene-1-carboxylate (0.21 g) as a colorless oil. 1H NMR(300 MHz, CDCl3) d: 11.71 (s, 1H), 7.33-7.16 (m, 5H), 6.92 (dt,J = 15.3, 6.8 Hz, 1H), 5.92 (dt, J = 15.3, 1.5 Hz, 1H), 4.19 (q,J = 7.1 Hz, 1H), 3.09-2.98 (m, 2H), 2.85-2.69 (m, 2H), 2.59-2.45(m, 2H), 2.39-2.25 (m, 2H), 1.73-1.56 (m, 4H), 1.30 (t, J = 7.1 Hz,3H). LCMS (ESI) m/z: 328.37 [M+H]+. The oil was dissolved in a mixture of THF (2 ml) and EtOH (1 ml) and to the obtained solution 2 N NaOH (0.92 ml, 1.84 mmol) was added. The mixture was stirred for 16 h at rt followed by stirring for 5 h at 50 C. The reaction mixture was cooled to rt and acidified to pH 4 with 1 N HCl. The solvents were evaporated and the residue was partitioned between DCM and water. The organic layer was dried over Na2SO4, evaporated, and the residue was chromatographed on silica gel (MeOH in DCM, 1:20) to give an oily solid. The solid was triturated with EtOAc petroleum ether mixture (1:4), filtered, and dried in vacuo to give the product 3 (44 mg, 14%, calculated with respect to 13) as white crystals.

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; Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4314 – 4329;,
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. 4891-38-7, name is Methyl Phenylpropiolate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C10H8O2

General procedure: (ESI) calcd for C20H16F3N4O2 [M+H]+ 401.12253, found 401.12283. Methyl 4-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate (11): typical procedure To a solution of ethyl o-mesitylsulfonylacetohydroxamic acid (78.5 g, 0.275 mol) in 1,4-dioxane (69 mL) was added a 70% aqueous solution of hydrogen perchlorate (28.5 mL, 0.330 mol), and the mixture was stirred at 0C for 0.5 h. After the addition of ice-water, the precipitate was collected. The cake was dissolved in dichloromethane (229 mL) and dried over Na2SO4. To the mixture was added a solution of 3-methoxypyridine (25.0 g, 0.229 mol) in dichloromethane (229 mL). After stirring at room temperature for 1 h, the mixture was concentrated in vacuo. To a solution of the resulting material in 10% DMF-THF (253 mL) was added potassium carbonate (63.0 g, 0.458 mol) and methyl 3-phenylpropiolate (18.0 g, 0.115 mol) at room temperature. After the addition of DMF (217 mL), the mixture was stirred at room temperature for 20 h. Water was added, and then the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, and then dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give methyl 4-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate 11 as a yellow solid (11.7 g, 36%, two steps).

According to the analysis of related databases, 4891-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Umei, Kentaro; Nishigaya, Yosuke; Kondo, Atsushi; Tatani, Kazuya; Tanaka, Nobuyuki; Kohno, Yasushi; Seto, Shigeki; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2635 – 2642;,
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. 538-23-8, name is Propane-1,2,3-triyl trioctanoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Propane-1,2,3-triyl trioctanoate

A mixture of two types of medium-chain fatty acid triglycerides (C8:0: tricaprilin and C10:0: tricaprin) is commercially available, and it can be used as a reaction material. Thus, this mixed medium-chain triglyceride was prepared at a ratio of 1 : 1 as a reagent. Then, two types of medium-chain fatty acid ester forms were synthesized in hexane from a free astaxanthin. That is to say, 2 mg of a free astaxanthin (manufactured by Sigma), 300 mg of tricaprilin and 300 mg of tricaprin were placed in a brown glass bottle. Twelve ml of n-hexane was added thereto, and three hundred mg of immobilized lipase prepared by the method described in the example of lipase immobilization and 30 muL of water were further added thereto and stirred fully afterwards. Thereafter, while stirring, reaction was carried out at 45C. Three days later, the reaction product was taken out, and the composition ratio of astaxanthin was analyzed by HPLC. As a result, the composition ratio was 81.4% astaxanthin, 9.5% C8 monoester, 9.1% C10 monoester, and less than 1% diester.

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 538-23-8.

Reference:
Patent; SUNTORY LIMITED; EP1500645; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19397-74-1, name is Ethyl 4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylate, 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 19397-74-1, Application In Synthesis of Ethyl 4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylate

The compound 4,5-dihydronaphthalene [1,2-b]thiophene-2-carboxylic acid ethyl ester (0.5 g, 1.94 mmol) and benzoyl peroxide (5 mg) obtained by the method of 14b) were dissolved in dry. In a solution of CC14 (8 mL), NBS (0.52 g, 2.9 mmol) was. The reaction solution was refluxed while being irradiated with a 200 W fluorescent lamp, and the generated hydrogen bromide gas was purged with a nitrogen stream, and the reaction was further refluxed for 1 hour. The reaction was completed to completion by TLC, and the reaction mixture was cooled, filtered and concentrated to give a crude product.With ethyl acetate /Recrystallization from n-hexane gave a yellow solid, 0.43 g.The yield was 87.2%.

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, Ethyl 4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Peking University; Jiangsu Enhua Pharmaceutical Co., Ltd.; Zhang Liangren; Wang Kewei; Yang Taoyi; Xue Yu; Li Qing; Zhang Guisen; (35 pag.)CN108727416; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 17205-02-6,Some common heterocyclic compound, 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, molecular formula is C7H12O3, 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.

Ethyl 3-hydroxycyclobutane-1-carboxylate (4 g, 27.4 mmol, 1.0 equiv) was dissolved in N,N-dimethylformamide and cooled to 0 C. NaH (60 %) (1.66 g, 41.6 mmol, 1.5 equiv) was added portion wise and the reaction mixture was stirred at 0 C for 24 hours.1-(chloromethyl)-4-methoxybenzene (5.24 g, 33.3 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (0-30 % EtOAc in Hexane) to afford product 3.1.19a (4.82 g, 65.8 % yield). LCMS (mlz): 265.5 [M+H]. 1H NMR (400 MHz, DMSO) 6 7.27 – 7.21 (m, 2H), 6.94 – 6.84 (m, 2H), 4.29 (s, 2H), 4.12-3.99(m, 2H), 3.99-3.83(m, 1H), 3.74(s, 3H), 2.66 (tt, J= 9.7, 8.0 Hz, 1H), 2.44-2.32 (m, 2H), 2.22-1.96 (m, 2H), 1.21-1.14 (m, 3H).

The synthetic route of 17205-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics