Author: Jessica.F

Related Products of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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.

Tributyltin methoxide (28.3 mL, 98 mmol), the product of preparation 8 (15.0 g, 65mol), isopropenyl acetate (10.8 mL, 98 mmol), palladium (II) acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100C for 5 hours. After cooling, the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90mL), and stirred for 15 minutes. The mixture was filtered through Arbocele and the organic phase was separated and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with diethyl ether : pentane, 0: 100 to 25: 75, followed by dichloromethane to give the title compound as a pale yellow oil in 94% yield (12.6 g). 1H NMR (400MHz, CDCI3) : 6 : 2.15 (3H, s), 3.61 (2H, s), 3.69 (5H, s), 7.10-7. 13 (2H, m), 7.19 (1H, d), 7. 30 (1H, t). LRMS ESI : m/z 229 [M+Na] +.

The synthetic route of 150529-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC; WO2005/92860; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61367-07-5,Some common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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.

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (4.08 g) obtained in Reference Example 2(1) is suspended in chloroform (50 ml), and thereto is added triethylamine (8.8 ml) under ice-cooling. Subsequently, a solution of 3-chloropropanesulfonyl chloride (3.35 ml) in chloroform (20 ml) is added dropwise over 20 minutes under the same temperature. After stirring for 2 hours at room temperature, 5 % hydrochloric acid is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropylamine, and filtered to collect precipitates to give methyl trans-4-{[(3-chloropropyl)sulfonyl]amino}cyclohexanecarboxylate (6.14 g). APCI-MS M/Z:315/317[M+H]+.

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

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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: In a glove box, add a ruthenium complex Il (0.75 mg, 0.001 mmol),Potassium methoxide (3.5 to 70 mg, 0.05 to 1 mmol), tetrahydrofuran (1 to 10 mL), and ester compounds (0.5 to 10 mmol).After sealing the autoclave, remove it from the glove box and fill it with hydrogen to the required pressure.The reaction vessel was stirred at room temperature for 16 to 24 hours.After slowly releasing excess hydrogen, the reaction solution was depressurized to remove the solvent, and the residue was purified by a short column of silica gel to obtain an alcohol compound.The results are shown in Table 7.

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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 6933-47-7 as follows. HPLC of Formula: C9H11NO2

Intermediate 7.5.24-tert-Butoxycarbonylamino-2-methyl-benzoic acid methyl esterTo a stirred solution of intermediate 7.5.1 (1.5 g) in dioxane (15 ml) at 10 C. was added a solution of Boc anhydride (2.2 g) in dioxane (15 ml) dropwise and the reaction allowed to warm to rt. After 3 h, dimethylaminopyridine (catalytic amount) was added. After overnight stirring, the mixture was concentrated, and the residue was purified by flash chromatography (dichloromethan with ethanol gradient 0 to 4%) affording 0.69 g of the title compound.ESI mass spectrum: [M+H]+=266

According to the analysis of related databases, 6933-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/28938; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 6065-82-3, 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. 6065-82-3, name is Ethyl diethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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. 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. COA of Formula: C8H14O2

Example 71 (2S)-1-{1-[2-(4-Fluoro-3-methyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60, steps A] to C] starting from 4-chloromethyl-5-methyl-2-(4-fluoro-3-methyl-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 4-fluoro-3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. The title compound was obtained as a white gum. MS (ISP): 397.3 (MH+).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); 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. 106-32-1, name is Ethyl octanoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl octanoate

To the 1000 mL four-necked flask was added hydroxylamine hydrochloride(48.7 g, 0.70 mol, 1.4 eq), water (50 g),Ethanol (200 g, 2.3X), stirred at room temperature until hydroxylamine hydrochloride was dissolved,Then joinEthyl octanoate(86.7 g, 0.5 mol, 1.0 eq), Stirred at room temperature to form a two-phase system, and then cooled to 5 ~ 10 ,Slowly add 40% KOH (168 g, 1.2 mol, 2.4 eq), Dripping finished, and then heated to 50 ~ 55 , insulation reaction 3 h,GC in the control of n-octanoic acid ethyl ester raw materials disappeared, stop the reaction,Cooled to 5-10 C, concentrated hydrochloric acid (90 mL) was added slowly,Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from benzene,A white flocculent solid was 78.8 g, yield 91.1%

According to the analysis of related databases, 106-32-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou Tianhua Pharmaceutical Co., Ltd.; Li Guangwen; (7 pag.)CN106966925; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 88709-17-5, 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. 88709-17-5 name is Ethyl 2-ethoxy-4-methylbenzoate, 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.

The reaction kettle was charged with ethyl 4-methyl-2-ethoxybenzoate (2.08 g, 10 mmol), isopropanol (100 mL, 1.33 mol), 30% hydrogen peroxide (13.6 mL, 12 mmol), and copper fluoride (24.9 mg, 0.3 mmol), bis- (diphenylphosphine) ethylamine (132.9 mg, 0.3 mmol), charged with 2.0 MPa of CO, heated to reflux, and stirred for 10 hours. After cooling to room temperature, a 2 mol / L potassium hydroxide aqueous solution (30 mL) was added to the reaction solution after depressurization, and the reaction was stirred at 40 C for 6 hours. Then, cyclohexane (50 mL × 3) was added to wash the reaction solution. The reaction solution was neutralized with hydrochloric acid to a pH of 7 , Concentrated under reduced pressure to about 50 mL, acidified with hydrochloric acid to pH 3, a yellow solid precipitated, filtered, and the residue was recrystallized from toluene-petroleum ether to obtain a white solid intermediate (I) (1.87 g, yield: 74.1%).

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

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yu Rui; Hong Xuming; Zheng Min; Shao Qingling; (8 pag.)CN110483292; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 29006-01-7, name is Methyl 4-methoxybutanoate, 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 29006-01-7, Quality Control of Methyl 4-methoxybutanoate

26 6-Bromo-3-(3-methoxypropyl)-[1,2,4]triazolo[4,3-a]pyridine; A mixture of 18. 80 g of (5-bromopyridin-2-yl) hydrazine (77992-44-0] and 14. 54 g of methyl 4-methoxybutyrate [29006-01-7] is heated to reflux over 16 hours. The reaction solution is subsequently cooled and purified by means of flash chromatography (SiO2 60F). The title compound is identified on the basis of the Rf value

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; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); 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 2318-25-4 as follows. category: esters-buliding-blocks

Preparation Example A-12. 2-(2-Cyanoethyl)-3,3-diaminopropenoic acid ethyl ester (1-Ethoxyformimidoyl) 1-acetic acid ethyl ester hydrochloride (50g, 0.26mol) was suspended in an ammonia-ethanol solution (300mL; prepared by saturating ethanol with ammonia gas at room temperature), which was then stirred at room temperature for 4 hours. After the reaction was completed, the precipitated salt was removed by filtration, and the filtrate was concentrated in vacuo at room temperature to reach 1/3 of the amount. Hydrochloric acid-methanol (130mL; hydrochloric acid content:7.5percent) was added to this filtrate, the solution was then concentrated under a reduced pressure to obtain 3,3-diamino-acrylic acid ethyl ester hydrochloride (40g, 0.24mol, 92percent) as a solid. The resulting 3,3-diamino-acrylic acid ethyl ester hydrochloride (2.2g, 13.2mmol) was suspended in tetrahydrofuran (40mL), triethylamine (2mL, 14.3mmol) and acrylonitrile (1.2mL, 19.3mmol) were added thereto, and the solution was refluxed for 6 hours. After the reaction was completed, the resulting triethylamine hydrochloride was filtered, and the filtrate was concentrated to obtain the title compound (0.6g, 3.3mmol, 25percent). 1H-NMR Spectrum (CDCl3) delta (ppm) :1.26 (3H, t, J=7.2Hz), 2.42-2.49 (2H, m), 2.50-2.57 (2H, m), 4.12 (2H, q, J=7.2Hz), 4.22 (2H, brs), 6.45 (2H, brs).

According to the analysis of related databases, 2318-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics