Category: esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)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 252881-74-6, HPLC of Formula: C13H27NO5

To 13-amino-4, 7, 10-trioxadodecanoic acid tert-butyl ester (0.80 g, 2.89 mmol) in 30 mL of dioxane was 10 ml of HCl (36%) with stirring. After 0.5 h TLC analysis revealed that the reaction was complete, the reaction mixture was evaporated, and co-evaporated with EtOH and EtOH/Toluene to form the title product in HCl salt (>90%pure, 0.640 g, 86%yield) without further purification. ESI MS m/z+ C 9H 20NO 5 (M+H) , cacld. 222.12, found 222.20.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
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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. 33155-58-7, name is tert-Butyl 2-(4-Bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a stirring solution of 2-(5-chlorothiophen-2-yl)-4-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1 eq.)in toluene (1.5 ml) was added Na01Bu (1.6 eq.), tert-butyl 2-(4-bromophenyl)acetate (1.5eq.) and BINAP (0.04 eq.). The resulting reaction mixture was degassed with argon for a period of 10 min. and Pd2dba3 (0.02eq.) was added and the mixture was degassed again. The reaction mixture was heated at 100C for16 h. At completion, the reaction mixture was concentrated and poured in DMF (2 mi).The inorganics were filtered and the residue was purified by prep-HPLC using aqueous ammonia method to give tert- butyl 2-(4-(2-(5-chlorothiophen-2-yl)-4-methyi-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)phenyl)acetate which was directly used for the next step. ).

According to the analysis of related databases, 33155-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; NARDI, Antonio; HESSLINGER, Christian; WO2015/18534; (2015); 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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 431-47-0

Trifluoroacetanilide (100 mg, 0.46 mmol), DMF (4 mL), potassium t-butoxide (153 mg, 1.37 mmol, 3 eq.) was added to the reaction mixture in turn, and stirred at room temperature for 5 minutes.After the potassium tert-butoxide was uniformly dispersed, methyl trifluoroacetate (0.19 mL, 1.84 mmol, 4 eq.) was slowly injected into the reaction flask, and after stirring at 60 C for 10 hours, stirring was stopped.Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution.The organic phases were combined, and the organic phase was dried over anhydrous magnesium sulfate.Magnesium sulfate was removed by filtration, and the solvent was evaporated to give purified N-(4-methoxyphenyl)-N-methyltrifluoroacetamide (88 mg, yield 83%).

According to the analysis of related databases, 431-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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. COA of Formula: C11H14O4

6,7-Dimethoxy-1-methylisoquinolin-3-ol CCH 18060 To a solution of methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 (23.82 g, 113.30 mmol) in acetic anhydride (57 mL) at 0 C. in a 1 L round-bottomed flask equipped with a magnetic stirrer under N2 was added perchloric acid (70% solution in water, 11.3 mL) over a period of 30 min. The reaction mixture was then allowed to warm up to RT, stirred for a further 45 min and diluted with Et2O (450 mL). The solid was then filtered and washed several times with Et2O (6*15 mL) to give after drying under vacuum a dark yellow solid (27.97 g, 74% yield). To a suspension of the above solid (11.09 g, 34.58 mmol) in H2O (60 mL) in a 500 mL 3-neck round-bottomed flask equipped with a dropping funnel and a magnetic stirrer in an ice bath was added dropwise conc. NH4OH (90 mL) and the reaction mixture was stirred at RT for 1 h, after which the solid was filtered and washed with cold water (4*15 mL). After drying under high vacuum, 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 was isolated as a yellow solid (7.53 g, 99% yield). MW: 219.24; Yield: 74%; Yellow solid; Mp ( C.): 283 (dec.). Rf: 0.2 (cyclohexane:EtOAc=2:1). 1H-NMR (DMSO d6, delta): 2.68 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 6.51 (s, 1H, ArH), 6.97 (s, 1H, ArH), 7.12 (s, 1H, ArH), 10.69 (broad s, 1H, OH). 13C-NMR (DMSO d6, delta): 20.3, 55.6, 55.7, 99.5, 103.6, 103.8, 116.2, 138.0, 147.1, 152.0, 153.3, 159.0. MS-ESI m/z (rel. int.): 220 ([M+H]+, 100).

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ExonHit Therapeutics SA; ALLERGAN, INC.; US2012/214837; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 4630-80-2, name is Methyl cyclopentanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl cyclopentanecarboxylate

General procedure: In the glove box, a conjugated boronic acid pinacol borate (1.2 mmol, 304.8 mg) was added to a Schlick reaction tube.Ferrous (0.03mmol), sodium tert-butoxide (0.9mmol), removed from the glove box, and added ethyl hexanoate under nitrogen atmosphere(0.3 mmol, 43.3 mg), ethanol (0.3 mmol), then 2 ml of toluene was added, and after stirring for 5 minutes, the reaction tube was placed at 100 C.The reaction in the pot was carried out for 24 hours. After the reaction is completed, ethyl acetate extraction is added to the system, and the product is obtained by column chromatography, and the yield is73%.

The synthetic route of 4630-80-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Liu Chao; He Zeyu; Zhu Qing; (10 pag.)CN109734737; (2019); 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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 3-(4-aminophenyl)acrylate

EXAMPLE 252 4-[14-(Trimethylsilyl)tetradecylamino]cinnamic acid A mixture of 5.0 g. ethyl 4-aminocinnamate, 9.14 g. of 14-(trimethylsilyl)tetradecyl bromide and 3.6 g. of powdered anhydrous potassium carbonate in hexamethylphosphoramide is heated for 20 hours at 60° C. The mixture is then cooled, diluted with water and extracted with ether. The combined ether extracts are dried, filtered and evaporated to provide ethyl 4-[14-(trimethylsilyl)tetradecylamino]cinnamate.

According to the analysis of related databases, 5048-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US4670421; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 13195-64-7, 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. 13195-64-7 name is Diisopropyl malonate, 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.

To a solution of diisopropyl malonate (500 mg, 2.65 mmol, 1 equiv) and nitroso benzene (313 mg, 2.92 mmol, 1 equiv) in absolute ethanol (1.25 mL, 2.2M), a saturated ethanolic solution of NaOH was added dropwise until the blue color of the solution turns pale brown. The reaction mixture was allowed to stir for 10 minutes and the solvent was removed under reduced pressure and the crude product was purified by column chromatography to afford 39 as viscous yellow colored oily liquid (449 mg, 61 percent).

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

Reference:
Patent; WILLIAM MARSH RICE UNIVERSITY; KATTAMURI, Padmanabha Venkatesh; KURTI, Laszlo; (181 pag.)WO2018/213572; (2018); 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 179688-27-8 as follows. Computed Properties of C15H23NO6

To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (Pfizer patent WO 96130347) in 50 ml of DMF at 0C was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55C for 45 m, cooled, diluted with methylene chloride, and treated at 0C with 200 ml of N/1 sodium hydroxide during 2 m. The organic layer was separated and washed at 0C with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) delta 3.02 (s, Me2N).

According to the analysis of related databases, 179688-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth Holdings Corporation; EP973746; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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. COA of Formula: C4H7BrO2

(2-Acetoxy-ethoxyimino)-[4-((1R,3R,7S)-9-bicyclo[3.3.1]non-3-yl-9-aza-bicyclo[3.3.1]non-3-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-acetic acid methyl ester (d26) To a suspension of d25 (331.0 mg, 0.672 mmol) in MeCN-DMF (2:1) (15 mL) was added 2-bromoethyl acetate (0.156 mL, 1.344 mmol) and K2CO3 (279 mg, 2.016 mmol) at a temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at a temperature of about 25 C. for 6 hr and 60 C. for 3 hr. The reaction mixture was diluted with water-saturated aqueous NaHCO3 (1:1), then extracted with AcOEt-CHCl3 (4:1) (x2). The combined organic phases were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting yellow amorphous solid was chromatographed (silica-gel 15 g, v/MeOH (10% concentrated NH4OH)=100/0?17/3) to provide 258.2 mg of d26 as a yellow solid. (Yield 66%) d26: 1H-NMR (300 MHz, CDCl3-CD3OD-DCl) delta: 1.28-3.05 (m, 27H), 3.89 (s, 3H), 4.02-4.13 (m, 2H), 4.13-4.25 (m, 1H), 4.26-4.31 (m, 2H), 4.47-4.53 (m, 2H), 6.37-6.54 (m, 1H), 7.39 (t, J=7.53 Hz, 1H), 7.79 (td, J=7.93, 1.37 Hz, 1H), 7.86 (dd, J=7.93, 1.51 Hz, 1H), 8.78 (d, J=8.69 Hz, 1H); LC/MS: m/z=579.4 [M+H]+ (Calc: 578).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 927-68-4, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Safety of Trimethyl methanetricarboxylate

N-benzyl-3-isopropyl-7-methoxy-6-(3-methoxypropoxy)tetralin-1-imine (1 g, 2.53 mmol) and trimethyl methanetricarboxylate (1.44 g, 7.6 mmol) were dissolved in diglyme (10 mL). The reaction mixture was stirred at 180 C in a microwave reactor for 30 minutes. Ethyl acetate (20 mL), followed by H2O (30 mL) were added to the reaction mixture. The separated organic layer was washed with H2O (2 x 20 mL), saturated aqueous brine solution (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by normal phase SiO2; chromatography (0 to 70 % EtO Ac/hexanes) to give methyl 1-benzyl-4-hydroxy-5-isopropyl-9-methoxy-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylate as a yellow oil (560 mg, 42% yield, m/z: 522 [M+H] observed).

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

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics