Month: June 2021

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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7ClO4S

7V-(3-Methyl-benzo[Z>]thiophen-2-yl)-2-carbomethoxy-ethanesulfonamide (600-A).; A solution of compound 757-A (1.0 g, 5.01 mmol) and pyridine (851 muL, 10.5 mmol) in dichloromethane (20 mL), cooled to 10 0C was treated with 3- chlorosulfonyl-propionic acid methyl ester (716 muL, 5.25 mmol) and stirred at ambient temperature for 18 h. The solvent was evaporated in vacuo, and the crude residue purified by flash column chromatography (SiO2), eluting with an ethyl acetate (10- 50%) in heptane gradient to afford 1.1 g of compound 600-A as an off white solid. 1H- NMR (DMSO-fe): delta 2.31 (s, 3H), 2.82 (t, 2H), 3.43 (t, 2H), 3.62 (s, 3H), 7.24-7.50 (m, 2H), 7.58-7.77 (m, IH), 7.80-7.95 (m, IH), 10.17 (s, IH); MS: m/z 314.1 (MH+).

The synthetic route of 15441-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2009/12430; (2009); A1;,
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Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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. Product Details of 110661-91-1

Under a N2 atmosphere, NaH (219 mg, 5.99 mmol, 60% dispersion in mineral oil) was added to a stirring suspension of fert-butyl 3-oxopiperazine-l-carboxylate (1 g, 4.99 mmol) in THF (20 mL) at 0C and stirred for five minutes. Ethyl 4-bromobutanoate (1.33 g, 5.99 mmol) was added at 0C. The reaction was stirred overnight. The reaction was quenched with several drops of methanol, diluted with ethyl acetate, and washed with H20, brine, and dried over magnesium sulfate. The organic layer was concentrated in vacuo which provided the crude material as a clear oil. The crude oil was purified by flash chromatography with ethyl acetate in hexanes as the eluent to afford Intermediate 23A (364 mg, 21%) as a clear oil. LCMS (method A): m/z 343.4 (M+H)+. lH NMR (CDC13): delta 4.06 (s, 2H), 3.63 (t, 2H), 3.42 (t, 2H), 3.36 (t, 2H), 2.26 (t, 2H), 1.84 (quin, 2H), 1.46 (s, 9H), 1.44 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110661-91-1, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
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Application of 3196-23-4, 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. 3196-23-4 name is Methyl 1-bromocyclohexanecarboxylate, 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.

General procedure: A mixture of 2.5 g of zinc, 5.53 g (25 mmol) of bromo ester 1, a catalytic amount (5 mg) of HgCl2, and 40 mL of benzene was heated for 3 h under reflux. The mixture was cooled, 10 mmol of aldehyde 4a-4i was added, and the mixture was heated for 2 h under reflux.After cooling, the mixture was treated with 5% aqueous acetic acid, the organic phase was separated and dried over Na2SO4, and the solvent was distilled off.The crystalline product (7a-7i) was recrystallized from ethyl acetate. Treatment of the residue with methanol led to crystallization of compound 11a-11d which was recrystallized from methanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-bromocyclohexanecarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Kirillov; Nikiforova; Vasyanin; Dmitriev; Russian Journal of Organic Chemistry; vol. 51; 4; (2015); p. 513 – 517; Zhurnal Organicheskoi Khimii; vol. 51; (2015); p. 530 – 534,5;,
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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. 1187318-53-1, name is 3-Bromo-5-fluoro-2-methyl-benzoic acid methyl ester, A new synthetic method of this compound is introduced below., name: 3-Bromo-5-fluoro-2-methyl-benzoic acid methyl ester

To a solution of methyl 3-bromo-5-fluoro-2-methylbenzoate (3.38 g, 13.7 mmol) in CCl4 (40 mL) at RT was added NBS (3.18 g, 17.9 mmol) and the reaction flask was purged with N2. After heating at 85 C for 5 m, AIBN (1.18 g, 6.87 mmol) was added, and the mixture was heated at 85 C overnight. The mixture was concentrated, diluted with H2O, and extracted with EtOAc. The organic phase was dried over Na2S04, filtered, and concentrated to give the crude product, which was purified using silica gel eluting with EtOAc in petroleum ether (0% to 1%) to give methyl 3-bromo-2-(bromomethyl)-5-fluorobenzoate (3.3 g, 74% yield) as an oil.

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; BIOTHERYX, INC.; CHAN, Kyle W.H.; CHOURASIA, Aparajita Hoskote; FUNG, Leah; MERCURIO, Frank; SULLIVAN, Robert; (0 pag.)WO2019/173224; (2019); A1;,
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Electric Literature of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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 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).

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); 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. 14064-10-9, name is Diethyl 2-chloromalonate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 14064-10-9

To a stirring solution of M-2 (0.30 g) in acetone (30 ml) at ambient temperature is added diethyl chloromalonate (0.149 g) and K2CO3 (0.194 g). The resulting mixture is stirred for 16 h and solvent removed in vacuo. The residue is suspended between EtOAc/ H2O (100 ml each), the layers shaken, the organic layer separated, dried over Na2SO4, and solvent removed in vacuo. The residue is suspended in hexane, sonicated and filtered, to afford 0.295 g title compound as a white solid. 1H NMR (DMSO) delta0.83, 1.15, 1.50, 2.68, 2.95, 4.21, 4.92, 5.61, 6.83, 7.26, 7.49, 7.91; IR (mull) 3286, 1747, 1696, 1674, 1643, 1538, 1510, 1334, 1296, 1290, 1260, 1225, 1186, 1028, 698, cm-1. MS (FAB) m/z 586 (MH+), 586, 569, 434, 384, 305, 265, 176, 92, 91, 86. Anal. Found: C, 61.09; H, 6.56; N, 7.03.

According to the analysis of related databases, 14064-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia & Upjohn Company; US6353023; (2002); B1;,
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 148547-19-7 as follows. category: esters-buliding-blocks

The compound 120a (1.0 g, 4.365 mmol) was dissolved in 1,4-dioxane (30 mL), and the compound 120b (2.22 g, 8.73 mmol), KOAc (1.5 g, 15.277 mmol), and PdCl2 were added. (dppf) (0.32 g, 0.436 mmol) and,Nitrogen was replaced three times, and then the reaction solution was stirred at 95 C for 16 hours. Cool to room temperature, add water (60 mL),Extracted with ethyl acetate (30 mL x 3), combined the organic layers and washed with water (30 mL x 2), dried over MgSO4, filtered and concentrated,The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-10%) to obtain a white off-white compound 120c, 3-methyl-4- (4,4,5,5-tetramethyl-1, Methyl 3,2-dioxaborolan-2-yl) benzoate (1.113 g, yield 92.4%).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
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Electric Literature of 15963-40-3,Some common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, molecular formula is C7H10O2, 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.

a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 mm to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-1-carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 Cand methanol (20 mL) was added slowly and the mixture was stirred for 30 mm at 25 C. The reaction mixture was cooled to -10 C and H202 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 mm) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SO3 aqueous. The resulting solution was diluted with water (300 mL) andthen extracted with ethyl acetate (2×300 mL) and the organic layers combined. The resulting mixture was washed with brine (2×300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3 -(hydroxymethyl)cyclobutane- 1 -carboxylate as colorless oil (6.6 g, 58%).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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Adding a certain compound to certain chemical reactions, such as: 541-16-2, name is Di-tert-Butyl malonate, 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 541-16-2, Safety of Di-tert-Butyl malonate

Step 1: Preparation of 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester, shown below To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred for 18 hours at room temperature and treated with a mixture of ice and water. The crude product was extracted with dichloromethane (3*) and sequentially washed with water (3*), and brine. The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography (100 g SiO2, 3% diethyl ether in hexane) to provide the desired product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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, Di-tert-Butyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/274648; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. name: Ethyl 2-bromo-3-methylbutanoate

4-fluoro-3-nitrophenol (500 mg, 3.18 mmol) was dissolved in DMF (6.365 mL) at room temperature. Cesium Carbonate (1244 mg, 3.82 mmol) was added followed by ethyl 2-bromo-3-methylbutanoate (0.574 mL, 3.50 mmol). The mixture was stirred at 60 C. Reaction left at 60 C overnight. Reaction was then diluted with water and a precipitate formed. The solid was filtered off and dried on high vacuum overnight to yield 83A (tan solid, 615 mg, 2.156 mmol, 67.7 % yield), yield). LC-MS Anal. Calc’d for Ci3Hi6FN05 285.10, Tr = 1.04 min (Method A) (Note: product does not ionize well). NMR (400 MHz, MeOH-d4) delta: 7.60 (dd, J=6.0, 3.3 Hz, 1H), 7.53 (dd, J=10.9, 9.3 Hz, 1H), 7.38 (s, 1H), 4.84 (d, J=4.8 Hz, 1H), 4.16 (dd, J=7.1, 2.8 Hz, 2H), 2.20-2.30 (m, 1H), 1.15-1.20 (m, 3H), 1.01 (dd, J=6.8, 4.6 Hz, 6H) 83B.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; (203 pag.)WO2016/210414; (2016); A1;,
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Ester – an overview | ScienceDirect Topics