Category: esters-buliding-blocks

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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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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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;,
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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;,
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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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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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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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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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Related Products of 6279-86-3, The chemical industry reduces the impact on the environment during synthesis 6279-86-3, name is Triethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

p-Methoxyaniline (123 mg, 1 mmol) was dissolved in dimethylformamide (1 ml).;Then, triethyl methanetricarboxylate (232 mg, 1 mmol) was added.;The mixture was heated for six hours at 170-190 C. The reaction was cooled to rt and treated with ethanol, filtered and washed with ethanol to yield 8 as a yellow solid (143 mg, 58%); mp 308-310 C; 1H NMR (500 MHz, DMSO-d6) delta 3.79 (s, 3H), 3.86 (s, 3H), 7.01 (d, J = 8.9 Hz, 2H), 7.40 (br s, 3H), 7.59 (d, J = 8.9 Hz, 2H), 12.01 (s, 1H), 12.63 (s, 1H), 16.67 (s, 1H); 13C NMR (125.7 MHz, DMSO-d6) delta 55.09, 55.38, 96.39, 104.22, 114.13, 114.51, 117.33, 122.13, 123.65, 129.58, 133.11, 154.53, 156.26, 161.98, 168.39, 171.37; Anal. for C18H16N2O5: Calcd C, 63.52; H, 4.74; N, 8.23. Found C, 63.66; H, 5.00; N, 8.09.

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, Triethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sabbah, Dima A.; Simms, Neka A.; Wang, Wang; Dong, Yuxiang; Ezell, Edward L.; Brattain, Michael G.; Vennerstrom, Jonathan L.; Zhong, Haizhen A.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7175 – 7183;,
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Electric Literature of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

ffl-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l-hvdroxy-3J-dimethylbutan-2- ylamino)acrylate.To a solution of 2,6-difluoro-5-iodonicotinic acid (4 g, 14.04 mmol, 1 equiv.) in toluene (30 mL) was added thionyl chloride (5.12 mL, 70.18 mmol, 5 equiv.) followed by DMF (0.5 mL). The reaction was stirred at 110 0C for 1 h. The reaction was concentrated. The residue was re-suspended in THF (15 mL) and added dropwise to a solution of ethyl-3- (dimethylamine)acrylate (2.1 mL, 14.04, 1,1 equiv.) and triethylamine (2.15 mL, 15.44 mmol, 1.1 equiv.) in THF (15 mL). The reaction was stirred at 67 0C for 2 h and cooled to 23 C. (5)-2-amino-3,3-dimethylbutan-l-ol (1.81 g, 15.44 mmol, 1.1 equiv.) was subsequently added and stirred at 23 0C for 30 min. The reaction was quenched with water (40 mL) and ethyl acetate (40 mL). The aqueous layer was extracted with ethyl acetate (2×40 mL), and the organics were dried and concentrated. The compound was purified via silica gel chromatography and concentrated to provide (5)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l- hydroxy-3,3-dimethylbutan-2-ylamino)acrylate Intermediate 80 (4.49 g, 66 %). Calcd for C17H21F2IN2O4 [M + H]+: 482.9.

The synthetic route of Ethyl 3-(dimethylamino)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIFULCO, Neil; CHOY, Allison, Laura; QUIROGA, Olga; SHERER, Brian; WO2010/136817; (2010); A1;,
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