Category: esters-buliding-blocks

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. 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-amino-3-chlorobenzoate

Example 42A Methyl 4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-chlorobenzoate (0510) (0511) To a solution of 1.50 g (3.82 mmol) of the compound from example 2A and 710 mg (3.82 mmol) of 172 methyl 4-amino-3-chlorobenzoate in 15 ml of 49 DMF were added, in small portions at RT, 430 mg (3.82 mmol) of 153 potassium tert-butoxide. The mixture was stirred at RT for 15 min. Subsequently, another 215 mg (1.91 mmol) of potassium tert-butoxide were added in small portions, and the mixture was stirred at RT for a further 2 h. Thereafter, the mixture was introduced into 40 ml of a 10% 83 aqueous citric acid solution while stirring, whereupon there was precipitation of solids. After diluting with water, the solids were filtered off, washed with water and dried under reduced pressure. The crude product thus obtained was purified by means of column chromatography (100 g of silica gel, eluent: cyclohexane/ethyl acetate 85:15, Biotage). 1.60 g (80% of theory, 98% purity) of the 173 title compound were obtained. (0512) 1H-NMR (400 MHz, DMSO-d6): [ppm]=10.96 (s, 1H), 8.14-8.08 (m, 3H), 8.07-8.02 (m, 2H), 7.94 (dd, 1H), 7.66-7.61 (m, 2H), 7.60-7.50 (m, 3H), 3.90 (s, 3H), 2.48 (s, 3H). (0513) LC/MS (Method 1, ESIpos): Rt=1.32 min, m/z=509/511 [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; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); A1;,
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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H16O3

INTERMEDIATE B-33Step 1 : ethyl 4-(5-bromopyridin-2-yloxy)cycIohexanecarboxylate (B-31)To a solution of 5-bromo-2-hydroxypyridine B-30 (1.0 g, 5.75 mmol) and ethyl 4- hydroxycyclohexanecarboxylate (990 mg, 5.75 mmol) in THF (50 mL) was added PPh3 (2.4 g, 9.150 mmol) and DIAD (1.8 mL, 9.14 mmol). The reaction mixture was stirred at RT for 17 h. The solution was then concentrated and purified by ISCO to yield ethyl 4-(5- bromopyridin-2-yloxy)cyclohexanecarboxylate as a colorless oil (1.16 g, 62percent yield, 3:2 trans:cis ratio).

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

105-53-3, name is Diethyl malonate, 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 105-53-3

Synthesis of 2,2-dially malonic acid diethyl ester; To a mixture of diethyl malonate (10 g, 62.5 mmol) and bromoalkane (14.25 g, 187.5 mmol) was added a concentrated solution of sodium ethoxide (8.6 g of sodium in 70 m L of ethanol) slowly with continuous stirring by maintaining the temperature in between 5-10 0C. After addition of sodium ethoxide, the reaction mixture was allowed to stir at the same temperature for another 1h after which the cold-water bath was removed and the mixture was allowed to stir overnight at EPO room temperature. The excess solvent was removed, the residue was added in water and extracted in ethyl acetate. The organic phase was dried over Na2SO4 and evaporated to give a light yellow liquid. The crude material was purified by vacuum distillation to get a colorless liquid.1H NMR (400 MHz, CDCI3): 1.24 (t, 6H), 2.64 (d, 4H), 4.18 (q, 4H), 5.07-5.14 (m, 4H), 5.59-5.73(m, 2H).Mass: 240 [M]+.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIAN INSTITUTE OF TECHNOLOGY BOMBAY; WO2006/117800; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 5121-34-6, These common heterocyclic compound, 5121-34-6, name is Methyl 2-amino-3-methoxybenzoate, 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 solution of compound 53 (22.4 g 123 mmol) in DMF (250 mL) was added N-bromosuccinimide (21.9 g, 123 mmol) portionwise at 0 C. The mixture was stirred at 0 C for 0.5 h. To the mixture was added water and extracted with EtOAc (500 mL x 2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired compound 54 (27.5 g, 86%) as a white solid.

Statistics shows that Methyl 2-amino-3-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 5121-34-6.

Reference:
Patent; GREEN CROSS CORP.GREEN CROSS CORPORATION; CHOI, SOONGYU; SONG, KWANG-SEOP; LEE, SUK HO; KIM, MIN JU; SEO, HEE JEONG; PARK, EUN-JUNG; KONG, YOUNGGYU; PARK, SO OK; KANG, HYUNKU; JUNG, MYUNG EUN; LEE, KINAM; KIM, HYUN JUNG; LEE, JUN SUNG; LEE, MIN WOO; KIM, MI-SOON; HONG, DONG HO; KANG, MISUK; (278 pag.)JP5876570; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 2216-94-6,Some common heterocyclic compound, 2216-94-6, name is Ethyl phenylpropiolate, molecular formula is C11H10O2, 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.

General procedure: Catalytic tests of Ni3N/NC or Ni/NC were performed as follows: 1,2-diphenylethyne (5.38mmol), Ni/NC or Ni3N/NC catalyst (7.8mol%, based on ICP results) and solvent (70mL) were mixed in a stainless-steel autoclave (100mL) equipped with an electric heating system and a magnetically driven mechanical stirrer. The reaction system was flushed with hydrogen three times and pressurized with hydrogen (2.0MPa), and then heated to 100C for hydrogenation. After the completion of reaction, it was allowed to cool to room temperature and the residual hydrogen was released. The solvent was removed under reduced pressure, and the crude products were purified by column chromatography on silica gel to withhold the catalyst. For the substrate scope, the semi-hydrogenation of alkynes was conducted using a similar method. For a typical run: the alkyne (0.3mmol), 7.8mol% Ni3N/NC-6/5-550 and ethanol (3mL) were placed in a glass vial (4mL) with cap, septum, and needle, and then two glass vials were sealed in a stainless steel autoclave (100mL) equipped with an electrical heating system, where a certain amount of ethanol was added to keep the same horizontal level of ethanol inside and outside the glass vials. Then, the reaction system was treated following the same steps as described above.

The synthetic route of 2216-94-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Xiaozhen; Wen, Xin; Nie, Shilin; Dong, Jie; Li, Jingde; Shi, Yongqing; Zhang, Huiling; Bai, Guoyi; Journal of Catalysis; vol. 382; (2020); p. 22 – 30;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 61837-46-5, The chemical industry reduces the impact on the environment during synthesis 61837-46-5, name is Methyl 2-bromo-4-methylpentanoate, I believe this compound will play a more active role in future production and life.

Example 37 2-(2,3-Dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid pyrazin-2-ylamide A stirred suspension of sodium hydride (60% dispersion in oil, 208 mg) in N,N-dimethylformamide (25 mL) at 0 C. was treated with a solution of 5-trifluoromethoxy-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide. The reaction mixture was stirred for 30 min at 0 C. and then 2-bromo-4-methyl-pentanoic acid methyl ester (prepared as in Example 9, 1.1 g) was added and it was stirred for 1 h at 0 C. It was then slowly allowed to warm to room temperature and stirred for another 3 h at room temperature. After this time, the reaction mixture was diluted with water and extracted with methylene chloride. The organic layers were combined and dried over sodium sulfate, filtered and the filterate concentrated in vacuo. The crude material was purified by column chromatography (silica gel) to afford 2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid methyl ester (1.0 g, 64%).

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-bromo-4-methylpentanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 139102-34-4, 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. 139102-34-4 name is Methyl 4-bromo-2-methoxybenzoate, 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.

Under the protection of nitrogen,Compound 46C (232 mg, 1 mmol),Methyl 4-bromo-2-methoxybenzoate (257 mg, 1.05 mmol),Palladium acetate (22.5 mg, 0.1 mmol), BINAP (62.5 mg, 0.1 mmol),The 1,4-dioxane solution of cesium carbonate (489 mg, 1.5 mmol) was heated to 110 C for 4 hours, then cooled to room temperature, quenched with aqueous solution, filtered, and extracted with ethyl acetate.Dry with anhydrous sodium sulfate,The compound was quenched under reduced pressure to give compound 46D (158 mg, 40% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 120-61-6, A common heterocyclic compound, 120-61-6, name is Dimethyl terephthalate, molecular formula is C10H10O4, 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.

The synthetic procedure of the probe is illustrated in the Scheme 1. Methanolic solution (10 ml) of terephthalic acid in the presence of con.H2SO4 (10:1) was refluxed for 6 h. The reaction mixture was cooled to room temperature and evaporated under pressure, provided a dirty white colour solid. The solid formed was extracted with DCM for at least 3 times in order to completely remove the impurities and dried using MgSO4. The solution was then filtered and evaporated to give milky white solid (1 mmol). Subsequently, it was re-dissolved in methanol followed by slow addition of hydrazine monohydrate (2 mmol) and allowed to reflux for 3 h. The obtained white solid (bis-hydrazine derivative) was filtered,washed with water and dried under vacuum. A hot-aqueous solution of bis-hydrazine derivative (1 mmol) was mixed dropwise with pyridine-2-aldehyde (2 mmol) and again refluxed at 80 C for2 h. The probe (BPTH) was obtained as a white puffy solid which was filtered and dried in vacuum.

The synthetic route of 120-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senthil Murugan, Arumugam; Abel Noelson, Enose Rajan; Annaraj, Jamespandi; Inorganica Chimica Acta; vol. 450; (2016); p. 131 – 139;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.

[01289] Step 1 : Synthesis of methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-5-chloro- 2-methylbenzoate[01290] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 4.6 mmol) and tert-butyl (2-oxoethyl)carbamate ( 1 .4 g, 8.8 mmol) in methanol ( 10 mL), acetic acid (0.027 g, 4.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.352 g, 4.68 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired product (0.62 g, 38 %).

The synthetic route of 294190-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2216-92-4, The chemical industry reduces the impact on the environment during synthesis 2216-92-4, name is N-Phenylglycine Ethyl Ester, I believe this compound will play a more active role in future production and life.

Example 35 1, 1-Dioxo-5-phenyl-1, 2, 5-thiadiazolidin-3-one sodium salt A. N-sulfamoylated-N-phenylglycine ethyl ester; A solution N-phenylglycine ethyl ester (1.0 g, 5.58 mmol) and TEA (1.69 g, 16. 7 mmol) in MeCN, 3mL is added dropwise to a freshly prepared solution of sulfamoyl chloride (5.58 mmol) in MeCN (5mL) over 20 min. The mixture is stirred at room temperature (RT) for 16 h. The solvent is evaporated and the residue is partitioned between EtOAc and water. The organic layer is dried over anhydrous sodium sulfate (Na2SO4) and evaporated. The residue is flash chromatographed on silica gel using 30% No. 50% EtOAc in hexanes as eluent to afford the N-sulfamoylated-N-phenylglycine ethyl ester as a yellow solid : [M+1] + = 259.

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, N-Phenylglycine Ethyl Ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2003/82841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics