Category: esters-buliding-blocks

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. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 4-(aminomethyl)benzoate

To a stirred solution of 5-chloro-2-hydroxybenzoic acid (0.57 g, 3.3 mmol) and tert-butyl 4-(aminomethyl)benzoate (0.72 g, 3.5 mmol) in dichloromethane (5 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.95 g, 5.0 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (0.76 g, 5.0 mmol), and triethylamine (0.46 mL, 3.3 mmol). After being stirred overnight, the reaction mixture was poured into sodium bicarbonate aqueous solution (50 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL*2). The combined organic layers were washed with brine (50 mL), dried (magnesium sulfate), and evaporated. The residue was purified by flush column chromatography on silica gel eluding with hexane/ethyl acetate (10/1) to afford 0.57 g (48%) of the title compound as white solids: 1H-NMR (CDCl3) delta 12.12 (1H, s), 7.99 (2H, d, J=7.9 Hz), 7.47-7.30 (4H, m), 6.97 (1H, d, J=8.4 Hz), 6.67-6.52 (1H, m), 4.68 (2H, d, J=5.7 Hz), 1.59 (9H, s).

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; Pfizer Inc; US2005/250818; (2005); 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. 105-53-3, name is Diethyl malonate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Diethyl malonate

[Reference Example 3] Production of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane 8.79 g (54.9 mmol) of diethyl malonate and 99 mL of toluene were added into a three-necked flask (300 mL), and thereafter, 20.5 mL (52.4 mmol) of a 20% sodium ethoxide ethanol solution was added thereto as a base. The obtained mixture was stirred at room temperature for 0.5 hours. Thereafter, 9.89 g (24.9 mmol) of cis-1,4-di-4-toluenesulfonyloxy-2-butene, which had been obtained by performing the same operations as those in Example 1 and then purifying the obtained compound by silica gel chromatography, was added to the reaction solution. The obtained mixture was stirred at room temperature for 3.5 hours, and thereafter, 59.9 mL of a 1 M sodium hydroxide aqueous solution was added to the reaction solution. The obtained mixture was stirred for 1 hour, and an organic layer was then separated. A water layer was re-extracted with 50 mL of toluene, and organic layers were gathered. The gathered organic layer was washed with 50 mL of water three times, and the resultant was then filtrated, while washing the residue with toluene. The obtained filtrate was concentrated at 45C under reduced pressure, so as to obtain 22.4 g of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane in the form of a crude product of a light yellow oily substance. This crude product contained 1.25 g of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane (yield: 24%) and 3.94 g of 1,1-di-ethoxycarbonyl-3-vinylcyclopentene (yield: 74%).

According to the analysis of related databases, 105-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; API Corporation; EP2537825; (2012); 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. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrN2O2

In a sealed glassware, a mixture of intermediate 3a and intermediate 3b (75/25) (10 g; 28.39 mmol), N-boc-2,3-dihydro-lH-pyrrole (6.86 mL; 39.75 mmol) and K2CO3 (11.8 g; 85.18 mmol) in 1,4-dioxane (250 mL) was bubbled with N2. Then, PPh3(1.49 g; 5.68 mmol) and Pd(OAc)2(640 mg; 2.84 mmol) were added. The reaction mixture was heated to 100C for 5h. The reaction mixture was cooled down to rt, poured onto water and extracted with EtOAc. The organic layer was decanted, washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue (21 g) was purified by chromatography over silica gel (irregular SiOH; 20-45 muiotaeta; 450 g; mobile phase: 62%> heptane, 3% MeOH (+10% NH4OH), 35% EtOAc). The pure fractions were collected and evaporated to dryness yielding 2.3 g (17%>, impure) of intermediate 16a and 8.2 g (59%) of intermediate 16a.

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 1245643-11-1.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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Synthetic Route of 10259-22-0, 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. 10259-22-0, name is Ethyl 3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step a1b: compound A5 (3-(3-methoxyphenyl)-N,N,2-trimethyl-3-oxopropanamide)To 2,2,6,6-tetramethylpiperidine (17.5 g, 125 mmol) in 50 ml dry THF were added dropwise 72 ml (115 mmol) of a n-buthyllithium solution in n-hexane (1.6 M) at -30 C. After 30 minutes of stirring, 5.0 g (50 mmol) N,N-dimethylpropionamide (A1) (dissolved in 50 mL dry THF) were added and the mixture was cooled to -70 C. and stirred for 1 h at this temperature. 22.5 g (125 mmol) ethyl-3-methoxybenzoate (dissolved in 30 mL dry THF) were slowly added dropwise and the resulting mixture was stirred for another 2 h at -70 C. After the mixture had been allowed to warm to RT, it was hydrolyzed by employing a diluted aqueous solution of HCl (36 mL). The mixture was then washed with diethyl ether several times. The combined organic layers were dried over MgSO4. The organic solvents were evaporated under reduced pressure and the remaining residue was dried in vacuo. CC (eluent: n-hexane/ethyl acetate (1:4)) yielded 6.5 g (55%) of A5 in form of a colorless oil.

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

Reference:
Patent; Gruenenthal GmbH; US2011/306793; (2011); A1;,
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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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 4-amino-3-bromobenzoate

General procedure: PCl5 (0.23 g, 1.1 mmol) was added to an ice-cold solution of compound 6 (0.30 g, 1 mmol) in ether (15 mL). The reaction mixture was stirred at room temperature for 2 h and then was concentrated under reduced pressure. The crude product was dissolved in THF (15 mL). The arylamine (1 mmol) and triethylamine (1.2 mmol) was added to the solution successively. The reaction mixture was stirred at room temperature for 2 h and then was then evaporated under reduced pressure. The residue was chromatographed on silica gel using ethyl acetate:petroleum ether (1:4). Pure fractions were collected and concentrated, giving the desired compound (7a-7o).

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhan, Peng; Chen, Xuwang; Li, Xiao; Li, Dongyue; Tian, Ye; Chen, Wenwen; Pannecouque, Christophe; De Clercq, Erik; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 5039 – 5045;,
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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. 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 42122-75-8

Reference Example 54: Methyl 5-(aminosulfonyl)-2-chlorobenzoate (compound S54) To methyl 5-amino-2-chlorobenzoate (16.2 g) in concentrated hydrochloric acid (40 ml)/acetic acid (120 ml) suspension, a sodium nitrite (7.6 g) aqueous solution (20 ml) was added under ice cooling and the mixture was stirred at that temperature for 45 minutes. Next, the inside temperature of the reaction vessel was cooled to – 5C, copper (II) chloride 2-hydrate (3.7 g) and a 21% sulfur dioxide in acetic acid solution (60 ml) were added, and the mixture was raised to room temperature and stirred at 12 hours. Under ice cooling, distilled water was added to the reaction solution, the mixture was stirred at that temperature for 30 minutes, and the precipitate was collected by filtration. The filtrate was dissolved in tetrahydrofuran (50 ml), 28% ammonia water (10 ml) was added under ice cooling, and the mixture was stirred at that temperature for 15 minutes. The tetrahydrofuran was distilled off in vacuo, then ethyl acetate/hexane was added. The precipitate was collected by filtration to obtain the title compound (10.9 g).

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 42122-75-8.

Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, 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. Recommanded Product: tert-Butyl propiolate

0.2mmol added benzenesulfonyl hydrazide in the reactor, 0.2mmol of t-butyl propiolate, 5.0 mol% palladium acetate, 5.0 mol% dppp, 0.4 mmol copper acetate, 15 mol% beta-aminopropionic acid,2.0mL DMF and DMAc mixed solvent (volume ratio [3: 1]). In a nitrogen atmosphere, heat to 80 C and continue stirring for 0.5h to stop the reaction and cool to room temperature.Washed with saturated NaCl, then extracted with ethyl acetate, dried,The solvent was removed by distillation under reduced pressure, and the crude product was separated by column chromatography to obtain the target product with a yield of 78%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13831-03-3, its application will become more common.

Reference:
Patent; Hunan University; Zhou Yongbo; Liu Lixin; Su Lebin; Dong Jianyu; Yin Shuangfeng; (9 pag.)CN110698368; (2020); A;,
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Related Products of 145576-28-9, 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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 4-methylenecyclohexanecarboxylate (0.15 g, 0.892 mmol) in diglyme (3 mL) was added a solution of sodium 2-chloro-2,2- difluoroacetate (0.544 g, 3.57 mmol) in 5 ml of diglyme via syringe pump at 0.5 ml/h at 150 C. The reaction was cooled to rt, then diluted with DCM and washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was chargedto a 40 g silica gel cartridge which was eluted with a 20 mm gradient of 0-20% EtOAc in hexane to yield ethyl 1,1-difluorospiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.09 – 4.19 (2 H, m), 2.29 -2.45 (1 H, m), 1.89 -2.03 (2 H, m), 1.55 – 1.72(5 H, m), 1.45 – 1.54(1 H, m), 1.31 – 1.39 (1 H, m), 1.21 – 1.30(3 H, m), 0.84 – 0.94 (1 H, m).

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 4-methylenecyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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. 106-32-1, name is Ethyl octanoate, A new synthetic method of this compound is introduced below., Product Details of 106-32-1

General procedure: In a typical run, a 50 mL stainless steel autoclave equipped with a transducer for online pressure monitoring was charged under air of Pd-pol (10.6 mg, Pd: 0.5 mol%), the substrate (carboxylic acid or ester, 1.0 mmol), bromobenzene (0.1 mmol, 15.7 mg) and alcohol (5.0 mL). The autoclave was then purged three times with hydrogen, then pressurized with 2 bars H2, set on a magnetic stirrer and heated to 40 C. After the minimum time needed to reach reaction completion, the autoclave was let to reach room temperature, the hydrogen was vented and the autoclave opened. When necessary, 3.0 mL diethyl ether was added to the mixture at the end of reaction in order to dissolve organic reactants and products. The catalyst was recovered by centrifugation. The yields were assessed by GLC analysis of the organic solution by using biphenyl (50.0 mg) as internal standard.

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:
Article; Dell’Anna, Maria Michela; Capodiferro, Vito Filippo; Mali, Matilda; Mastrorilli, Piero; Journal of Organometallic Chemistry; vol. 818; (2016); p. 106 – 114;,
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Related Products of 15441-07-3, 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. 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.

In a 100 mL round bottom flask, to a solution of methyl 3-(chlorosulfonyl)propanoate (187 mg, 1 mmol) and S-trans, trans-farnesyl-L-cysteine methyl ester (339 mg, 1 mmol) in THF (5 mL) was added N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol) dropwise. The solution was stirred at 0 0C for 30 min and then room temperature overnight. The mixture was diluted with ethyl acetate (60 mL) and washed by 0.5 N HCl (10 mL x 1), H2O (10 mL x 1) and brine (10 mL x 1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was dissolved in THF (3 rnL) and a solution Of LiOH-H2O (420 mg, 10 mmol) in H2O (2 mL) was added slowly at 0 0C. The reaction was left at room temperature overnight. The solution was then diluted with ethyl acetate and washed by 0.5 N HCl (10 mL x 1), H2O (10 mL x 2) and brine (15 mL x 1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was then further purified by preparative HPLC (100 mg, 22%) to yield Compound N-80. 1H-NMR (500 MHz, CD3OD): delta 1.50 (s, 3H), 1.51 (s, 3H), 1.57 (s, 3H), 1.61 (s, 3H), 1.86-1.89 (m, 2H), 1.95-2.00 (m, 4H), 2.01-2.06 (m, 4H), 2.65 (dd, J = 8.0, 14.0 Hz, IH), 2.71-2.76 (m, 2H), 2.84 (dd, J = 5.0, 14.0 Hz, IH), 3.13 (dd, J = 7.5, 13.5 Hz, IH), 3.24-3.29 (m, IH), 4.05 (dd, J = 5.0, 8.0 Hz, IH), 4.98-5.03 (m, 2H), 5.09-5.14 (t, J = 8.0 Hz, IH). 13C-NMR (125 MHz, CD3OD): delta 16.15, 16.30, 17.80, 25.95, 27.38, 27.79, 29.56, 30.44, 34.80, 40.78, 40.89, 49.82, 57.51, 121.64, 125.16, 125.46, 132.12, 136.27, 140.62, 174.04, 174.15; ES-MS: mass calcd for Chemical Formula: C21H35NO6S2 461.64. Found (M+) m/z 462.2, (M+Na) m/z 484.2.

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, Methyl 3-(chlorosulfonyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNUM BIOSCIENCES, INC.; STOCK, Jeffry, B.; STOCK, Maxwell; RAPOLE, Keshava; LEE, Seung-yub; VORONKOV, Michael; PEREZ, Eduardo; CHEN, Shuyi; CHEN, Jinglong; GORDON, Joel; WO2010/56778; (2010); A1;,
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