Tag: M.W=100-200

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. 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl (E)-3-Ethoxyacrylate

To a mixture of 19 (3.7 g, 21.9 mmol) and (E)-ethyl 3-ethoxyacrylate (4.7 g, 32.8 mmol) in DMF (76 mL) was added Cs2CO3 (10.7 g, 32.8 mmol) and the reaction was heated at 110 C for 15 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was washed with acetic acid to pH 4 and extracted with EA (100 ml) for three times. The extract was dried over Na2SO4. The crude product was purified by flash chromatography to afford the title compound (2.2 g, 45.9 %). 1H NMR (400 MHz, CDCl3) delta 9.56 (br, 1H), 8.01 (d, J = 8.0 Hz, 1H), 6.08 (d, J = 8.0 Hz, 1H), 4.37 (q, J = 7.2 Hz, 2H), 2.50 (s, 1H), 1.39 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 222 [M+H]+.

According to the analysis of related databases, 5941-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lu, Xiaoyun; Tang, Jian; Liu, Zhiyong; Li, Minke; Zhang, Tianyu; Zhang, Xiantao; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 26; 24; (2016); p. 5916 – 5919;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 178312-47-5, A common heterocyclic compound, 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, molecular formula is C9H14F2O2, 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.

Example 1; 4,4-Difluorocyclohexanecarboxamide A suspension of ethyl 4,4-difluorocyclohexanecarboxylate (2500 mg, 13 mmol) in ammonium hydroxide (28%, 50 ml) was stirred at 60 C. overnight. After removal of solvent, the residue was washed with water. The precipitate was obtained as product (white solid, 800 mg). 1H NMR (300 MHz, CDCl3): delta 5.31-5.45 (br, 2H), 2.02-2.27 (m, 3H), 1.92-2.02 (m, 2H), 1.72-1.87 (m, 4H). The mother liquor was acidified with 1N HCl to pH<1. The compound was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate, filtered, condensed. 4,4-difluorocyclohexanecarboxylic acid was obtained as a 1200 mg of white solid which was further converted to 4,4-difluorocyclohexanecarboxamide by following procedure. The synthetic route of 178312-47-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AstraZeneca AB; US2009/111830; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 816-27-3, category: esters-buliding-blocks

To 2-phenylacetohydrazide (39.5 g, 263 mmol) in ethanol (150 mL) was added ethyl 2- ethoxy-2-iminoacetate (39.5 g, 272 mmol) and diethyl ether (200 mL). The reaction mixture was stirred for 10 min and solid formed. The reaction mixture was stirred for 5 hours and diethyl ether (50 mL) was added. The resulting mixture was stirred for 17 hours The solid was filtered, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2- phenylacetyl)hydrazono)acetate as a white solid (59 g, 85 % yield). The filtrate sat for 5 days and additional white solid precipitated out. The solid was filtered and dried to give 2-amino-2-(2-(2-phenylacetyl)hydrazono)acetate as a white solid (4.8 g) (92% total yield). MS ES+ m/z 250.1 [M+H]+; NMR (400 MHz, DMSO-d6) delta 9.95 (d, J=17.18 Hz, 1H), 7.13-7.37 (m, 5H), 6.50 (d, 2H), 4.24 (dq, J=7.07, 10.86 Hz, 2H), 3.86 (s, 1H), 3.50 (s, 1H), 1.27 (dt, J=7.07, 17.43 Hz, 3H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANBARI, Jill Marinis; BERTIN, John J.; JEONG, Jae U.; (139 pag.)WO2018/154520; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 85953-29-3,Some common heterocyclic compound, 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate, molecular formula is C8H6ClFO2, 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.

20.85 g of methyl 2-chloro-4-fluorobenzoate were dissolved in 150 ml of N-methylpyrrolidone, 30.68 g of potassium carbonate and 9.38 ml of 3-methylpyrazole were added thereto, and the mixture was stirred at 120 C for 3 hours.. Additionally, thereto was added 1.79 ml of 3-methylpyrazole, and the mixture was stirred at 120 C for 3 hours.. The reaction solution was cooled, mixed with water, and extracted with EtOAc. The organic layer was washed with water and brine, and then dried over magnesium sulfate.. The solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane-EtOAc (20:1)) to obtain 9.25 g of methyl 2-chloro-4-(3-metyl-1H-pyrazol-1-yl)benzoate.

The synthetic route of 85953-29-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1445253; (2004); 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. 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H14O3

Sodium (7.13 g, 0.31 mol) was added to 500 mL of toluene. Then ethyl formate (22.9 g, 0.31 mol) and Compound 10b (60 g, 0.31 mol) were added dropwise to the above solution at a temperature of below 30 C. The reaction mixture was stirred at room temperature overnight. The solvent was concentrated, and the resulting residue was dissolved in 300 mL of ethanol, and then guanidine hydrochloride (29.45 g, 0.31 mol) was added thereto. The reaction was heated to reflux overnight. The solvent was concentrated and 100 mL of water was added to the residue, which was adjusted with 1N HCl to pH=2. The insoluble solid was collected and dried to obtain Compound 10c (30 g, Yield 44%). MS [M+1]+ 219.1.

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 32122-09-1.

Reference:
Patent; ZHEJIANG HISUN PHARMACEUTICAL CO., LTD.; Ding, Yili; Yang, Xuan; Yan, Qingyan; Bai, Hua; Cai, Lifeng; Smith, Kenneth; Chai, Jian; US2014/378488; (2014); A1;,
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. 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

5 g (38.8 mmol)2-chloro-5-aminopyridine and7.28 (38.8 mmol)5- (methoxymeth) -2,2-dimethyl-1,3-dioxo-4,6-dione was suspended in100mLIsopropanol,Heated to reflux for 2 hours. TLC detection, after the end of the reactionDry solvent to obtain product l0.5g, light yellowish solid, yield 95.8%

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; Beijing Foreland Pharma Co., Ltd; Zhang, Xingmin; Wang, Ensi; Niu, Shengxiu; Guo, Jing; Dai, Zhuolin; Zheng, Nan; Ji, Qi; Li, Qinyan; Liang, Tie; (109 pag.)CN104411706; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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: C9H11NO3

Description 20: Methyl 4-{[(2-fluorophenyl)carbonyl]amino}-2-(methyloxy)benzoate; Methyl 4-amino-2-(methyloxy)benzoate (10.0 g, 55.2 mmol) was suspended in dichloromethane (50 ml_), cooled in an ice bath and treated dropwise with diisopropylethylamine (10.57 ml_, 60.8 mmol) followed by 2-fluorobenzoyl chloride (7.25 ml_, 60.8 mmol). The mixture was allowed to warm to room temperature and stirred under argon for 2.5 hours. The solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine. The ethyl acetate layer was separated. A solid came out of solution upon standing. This was collected by filtration to give the title compound. LC/MS (ES+ve): [M+H]+ at m/z 304 (C16H14FNO4 requires [M+H]+ at m/z 304).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/138033; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 37722-82-0, A common heterocyclic compound, 37722-82-0, name is Methyl 3-Hydroxycyclohexanecarboxylate, molecular formula is C8H14O3, 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 the solution of methyl 3-hydroxycyclohexanecarboxylate AA53 (25.7 g, 0.163 mmol) in dichloromethane (250 mL) was added Dess-Martin periodinane (69.0 g, 0.163 mmol) over 20 minutes at 0 . After stirred at room temperature for 3 hours, the mixture was filtered. The filtrate was washed with saturated sodium bicarbonate aqueous solution (200 mL) for three times, brine (200 mL) , dried over Na2SO4 (s), filtered and concentrated to give a residue, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 15 : 1 to 6 : 1) to give the title compound (20.5 g, 82 %yield) as colorless oil.1H NMR (400 MHz, CDCl3) delta 3.70 (s, 3H) , 2.84 -2.76 (m, 1H) , 2.54 (d, J = 10.4 Hz, 2H) , 2.37 -2.27 (m, 2H) , 2.13 -2.02 (m, 2H) , 1.90 -1.70 (m, 2H) .

The synthetic route of 37722-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; JIANG, Yimin; WAN, Zhao-Kui; CHEUNG, Wing Shun; LIU, Qian; DENG, Gang; LIANG, Chao; (230 pag.)WO2019/214610; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6627-89-0,Some common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, molecular formula is C11H14O3, 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 0.48 mL (3.8 mmol) of 4-bromo-lH-indole in 1 mL of THF was added to a suspension of 0.15 g (6.3 mmol) of NaH in 5 mL of THF, followed by 1.2 mL (6.3 mmol) of tert-butyl phenylcarbonate. The reaction solution was stirred 18 h, then quenched with1 mL of iPrOH, poured into 100 mL of Et2O and washed twice with a saturated aqueous solution of NH4Cl and thrice with water. The organic solvent was removed in vacuo and the residue was purified by flash chromatography eluting with neat hexane to yield the title compound. MS (M-BOC+2H)+ 196.

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

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1Atert-Butyl 1-(3-bromobenzyl)cyclopropanecarboxylate; Under argon, 14.8 ml (105.48 mmol) of diisopropylamine were initially charged in 66 ml of dry THF, and the mixture was cooled to -40 C. 42.2 ml (105.48 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 10.0 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 17 ml of THF was added. After 4 h of stirring at -78 C., a solution of 19.34 g (77.36 mmol) of 3-bromobenzyl bromide in 17 ml THF was added. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on 750 g of silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 13.3 g (60.7% of theory) of the title compound.GC-MS (Method 1): Rt=5.94 min; m/z=256 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.46 (s, 1H), 7.38 (m, 1H), 7.25 (m, 2H), 2.82 (s, 2H), 1.28 (s, 9H), 1.08 (q, 2H), 0.87 (q, 2H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics