Category: esters-buliding-blocks

Application of 69812-51-7, 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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 102; 4-(3-Cyclopentyl-indazole-1-sulfonyl)-benzoic acid methyl ester; Combine 3-Cyclopentyl-lH-indazole (2.168 g 11.640 mmole) with triethylamine (3.526g, 34.92 mmoles) in 50 mls of dichloromethane. Dissolve 4- Chlorosulfonyl-benzoic acid methyl ester (4.085g, 17. 460mmole) in dichloromethane 50ml and add drop wise to solution at 0 C. Stir the reaction is for 12 hrs. Dilute the reaction and wash with NaHC03. Dry organic layer over MgS04 and concentrate. Purify the residue via column chromatography with a mixture of ethyl acetate and hexanes to isolate 2.046g (Yield=48. 5%) of the title compound: MS ES+385.3.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-chlorosulfonylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
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Electric Literature of 927-68-4, A common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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 50; 2-(Acetyloxy)ethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-(2-thienyl)-1,6- dihydropyridazine-4-carboxylate; A mixture of the title product of Preparation 35 (0.15g, 0.42 mmol), potassium carbonate (0.17g, 12.63 mmol) and 2-bromoethylacetate (77.2 mg, 0.46 mmol) in dimethylformamide (4 ml) were heated at 50C for 4h. Once at room temperature, solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (CH2CI2:MeOH 99: 1 as eluent). 0.13 g (68%) of the desired final product were isolated. m. p.: 161.0-161.6C No. (DMSO-d6): 1.4 (t, J=7.0 Hz, 3 H) 1.9 (s, 3 H) 2.2 (s, 2 H) 3.4 (m, 3 H) 3.9 (m, 2 H) 4.2 (q, J=7.0 Hz, 2 H) 7.0 (m, 2 H) 7.3 (d, J=5.0 Hz, 1 H) 7.6 (d, J=5.0 Hz, 1 H) 8.3 (s, 1 H) 8.3 (d, J=5.0 Hz, 1 H) 9.0 (s, 1 H)

The synthetic route of 927-68-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL PRODESFARMA, S.A.; WO2005/123693; (2005); 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. 205448-64-2, name is Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate

After heating biphenylphenoxybenzene (360 mL) to 175 C, Compound 3 (30 g, 89.47 mmol, 1 eq) was added portionwise at 175 C over 20 min. Stirring was continued at 175 C for another 2 h. The reaction mixture was cooled to room temperature (l6C), and petroleum ether (500 mL) was added. The resulting solid was filtered, and the filter cake washed with 100 mL of methyl tertiary butyl ether, dried under vacuum, and purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, Eluent of 0-10% CH30H/CH2Cl2 50 mL/min) to give Compound 4 as a yellow solid (6 g, 27.3% yield). NMR (400 MHz, DMSO-d6) delta 11.70 (br s, 1H), 8.43 (s, 1H), 7.86 (br d, 1H), 7.02 (s, 1H), 5.99 (d, 1H), 3.89 (s, 3H), 3.81 (s, 3H); MS (El) for C12H11NO4, found 233.9 (MH+).

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; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
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Reference of 37466-90-3, 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B: Preparation of 1H-benzo[d]imidazole-6-carboxylic acid ethyl ester 40 g of 3,4-diaminobenzoic acid ethyl ester (0.22 mol) and 200 mL formic acid were added to a three-necked bottle. After refluxing for 7 h, the reaction was completed. After concentration under reduced pressure, the ice water was poured into the residual solution. The resulting mixture was adjusted to pH 7 with sodium hydroxide. After sucking filtration, the filtrate was extracted with dichloromethane thrice, dried with anhydrous sodium sulfate, and decolored with active charcoal. Then the solution was concentrated under reduced pressure to get a white solid (29.6g). Yield: 70.2%. MS: 191 (M+1)

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, Ethyl 3,4-diaminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang J & Health Pharmaceutical Co., Ltd.; EP2468730; (2012); A1;,
Ester – Wikipedia,
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3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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. Formula: C7H12O3

REFERENCE EXAMPLE 1 Preparation of 2-bromomethylcyclopropanecarboxylic acid ethyl ester (2-formyl)cyclopropanecarboxylic acid ethyl ester (14.2 g, 0.10 mol) was dissolved in methanol (200 ml). The solution was cooled to 0 C., and sodium borohydride (3.8 g, 0.10 mol) was added. The mixture was stirred for 20 minutes. After distilling off the solvent, a saturated sodium chloride aqueous solution was added thereto. The product was extracted with chloroform, then dried and concentrated. Then, it was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, yield: 99%). The (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, 0.1 mol) was dissolved in N,N-dimethylformamide (150 ml), and triphenylphosphine (25.9 g, 0.1 mol) was added thereto at room temperature. The mixture was stirred for 10 minutes. After cooling the mixture to 20 C., bromine (15.8 g, 0.1 mol) was dropwise added thereto over a period of 10 minutes. One hour later, the reaction mixture was added to a saturated sodium hydrogen carbonate solution, and the product was extracted with ethyl ether. It was dried, concentrated and then purified by column chromatography (hexane:ethyl acetate=5:1) to obtain (2-bromomethyl)cyclopropane carboxylic acid ethyl ester (15.3 g, yield: 74%). 1 NMR(CDCl3) delta0.9-1.0(m, 1H), 1.27(t, J=7.6 Hz, 3H), 1.3-1.5(m, 1H), 1.6-1.7(m, 1H, 1.8-2.0(m, 1H), 3.3-3.4(m, 2H), 4.25(q, J=7.6 Hz, 2H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Glass Company, Ltd.; US5416231; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 106685-41-0, 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 106685-41-0 as follows.

A round-bottom flask is loaded with adapalene methyl ester (7 g; 16.41 mmol), THF (42 ml), water (7 ml) and a 50% w/w sodium hydroxide aqueous solution (1.44 g; 18.05 mmol). The mixture is refluxed for 6 hours, then added with water (133 ml) and THF is distilled off to a residual content of approx. 5% w/w, heated to a temperature of about 80C until complete dissolution of the solid, then cooled to 15C. The crystallized product is filtered and dried under vacuum in a static dryer at a temperature of 50C, thereby obtaining adapalene sodium salt (6.7 g; 15.42 mmol) in 94% yield.

According to the analysis of related databases, 106685-41-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dipharma S.p.A.; Lundbeck Pharmaceuticals Italy S.P.A.; EP1707555; (2006); A1;,
Ester – Wikipedia,
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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. 2177-70-0, name is Phenyl methacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Phenyl methacrylate

Example 7 2.5 mL of tetrahydrofuran solution of 3.0 mol/L concentration of methylmagnesium chloride was added to 10 mL of anhydrous tetrahydrofuran in a reaction vessel under an atmosphere of argon, and then 1.0 g of 3,3,5-trimethylcyclohexanone was added with stirring while the mixture in the reaction vessel was kept at a temperature of 50 C. or less, followed by stirring for another one hour at the same temperature with stirring. Then, 1.20 g of phenyl methacrylate was added drop wise into the reaction vessel, and then 1.74 g of N,N,N’,N’-tetramethylethylene diamine, and the reaction was carried out with stirring for 24 hours at a temperature of 60 C. After the reaction, an aqueous saturated solution of ammonium chloride was added to the resulting reaction mixture, and the desired product was extracted with ethyl acetate. The obtained organic layer was subjected to gas chromatographic analysis. As a result, the yield of 1,3,3,5-tetramethylcyclohexyl methacrylate was found to be 18.0 mol %.

The synthetic route of 2177-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HONSHU CHEMICAL INDUSTRY CO., LTD.; US2006/167305; (2006); A1;,
Ester – Wikipedia,
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Application of 110661-91-1, 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. 110661-91-1, name is tert-Butyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate (20 g, 53 mmol) in DMF (100 mL) at 0 C. was added KOtBu (7.73 g, 69 mmol). The mixture was stirred at 0 C. for 45 minutes, then tert.-butyl 4-bromobutanoate (15.4 g, 69 mmol) was added at 0 C. The reaction mixture was allowed to warm to room temperature and stir overnight. The mixture was portioned between ether and saturated aqueous NH4Cl. The organic solution was washed with water and saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The residue was taken into hot cyclohexane. The mixture was allowed to stand for 72 hours. The solvent was decanted and the residue was washed with cold cyclohexane. The solid was then dried under high vacuum to yield 4-(3-tert.-butoxycarbonyl-propoxy)-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-1a: 20.8 g). 1H NMR (400 MHz, CHLOROFORM-D) ppm 1.4 (s, 9H), 1.4 (t, J=7.1 Hz, 3H), 1.9 (m, 2H), 2.3 (t, J=7.5 Hz, 2H), 4.0 (t, J=5.9 Hz, 2H), 4.4 (q, J=7.1 Hz, 2H), 7.2 (m, 2H), 7.2 (m, 2H), 7.4 (m, 3H), 7.5 (m, 1H); m/z=519.0 (M+1).

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

Reference:
Patent; Pfizer Inc; US2006/241100; (2006); A1;,
Ester – Wikipedia,
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Application of 148547-19-7,Some common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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.

A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24. 88-MMOL), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 * 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methyl acrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o-tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 ML, 1M). The product is extracted with dichloromethane (2 * 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M+1 207. The structure is confirmed by : L H NMR spectroscopy.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63184; (2004); 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 35418-07-6 as follows. category: esters-buliding-blocks

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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