Category: esters-buliding-blocks

Reference of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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.

(b) 2-(S-Acetylthiomethyl)4-methylpentanoic acid Hydrolysis of 91.1 g of isobutyldiethyl malonate is accomplished by digesting a solution of the ester in 300 ml of methanol and 400 ml of 10% NaOH for 6 hours at 80 C. The solution is concentrated in vacuo to 400 ml. It is acidified with 10% aqueous HCl and product is extracted with ethyl acetate to yield 67.6 g of the diacid. This crystallized on standing. M.P. 94-95 C. The diacid is suspended in 400 ml of water and cooled to 5 C. Aqueous 40% dimethylamine (50 g) and aqueous 37% formaldehyde (35.7 g) are added in that order. The solution is stirred overnight and Mannich base solid product is filtered and dried in vacuo to yield 57.3 g. M.P. 134-137 C. with CO2 and dimethylamine given off. The Mannich base (57.3 g) is suspended in 200 ml of water and 43 g of 50% NaOH in 100 ml of water is added until pH is 9. This solution is heated on the steam cone under nitrogen overnight. It is neutralized with 10% HCl and product is extracted with ethyl acetate to yield 23.8 g. The crude unsaturated acid is chromatographed (twice) on 200 g of silica to give 21.6 g of pure acid.

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

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
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Electric Literature of 207346-42-7, 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. 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 70-1 (1.00 g, 5.34 mmol, 1 eq) and 70-lc (1.50 g, 8.02 mmol, 1.5 eq) in DCM (15 mL) were added Cu(OAc)2 (1.40 g, 8.02 mmol, 1.5 eq) and DIEA (1.30 g, 10.69 mmol, 1.8 mL, 2 eq). The mixture was degassed, purged with 02 for 3 times and stirred at 20C for 16 hr. The mixture was concentrated. The residue was dissolved in EA (10 mL) and washed with H20 (3 mL *3). The combined organic layers were washed with brine (3 mL *3), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to give 70-2 (650.0 mg, 1.96 mmol, 36.7% yield). 1H NMR (400 MHz, CDCl3) d 9.61 (br s, 1H), 7.79 (dd, 7 = 9.0, 11.1 Hz, 1H), 7.58 (d, J= 8.5 Hz, 2H), 7.25 (d, .7= 2.3 Hz, 1H), 7.10 (dd, 7= 6.9, 12.8 Hz, 1H), 3.92 – 3.88 (m, 3H)

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 2-amino-4,5-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (559 pag.)WO2019/222431; (2019); 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. 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

A mixture of methyl 2-oxocyclooctanecarboxylate (32.0 g, 174 mmol), methyl 3-amino-4-bromobenzoate (20.0 g, 87 mmol) and ethanol (120 mL) was heated to reflux, at an oil bath of 130 C, acetic acid (1.5 mL) was added and the mixture was reflux for 1.5 hours. Hot PPA (200 g, 120 C) was added to the reaction mixture carefully. The reaction mixture was heated at an oil bath of 130 C for 3 hours. After cooling for a while, ice (200 g), ethyl acetate (60 mL) and petroleum ether (60 mL) were added to the reaction mixture, the mixture was concentrated until 200 mL solvent was removed. Then water (600 mL) and ethyl acetate (60 mL) were added, the resulting mixture was stayed at room temperature overnight. A light brown solid was slowly formed. The mixture was filtered and the filtered cake was dried to give a light brown solid, which was placed into methanol (90 mL). SOCl2 (30 mL) was added dropwise with cooling with an ice-bath. The resulting mixture was heated to reflux for 4 hours, concentrated and treated with saturated NaHCO3 solution (60 mL) and ethyl acetate (30 mL), filtered and the filtered cake was dried to give desired product (6.6 g) as a pale white solid (21%).

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 46064-79-3.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; REN, Bo; WANG, Hexiang; WO2013/97226; (2013); A1;,
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Related Products of 706791-83-5,Some common heterocyclic compound, 706791-83-5, name is Methyl 3-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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 a 7 mL vial was added a carboxylic acid compound (332 mg, 1.2 mmol), methyl 3-amino-5-bromobenzoate (270 mg, 1.2 eq)EDCI (3.0 eq), HOBt (3.0 eq) and DIPEA (3.0 eq) were dissolved in DMF (0.3 M) and stirred at room temperature for 16 hRespectively. After completion of the reaction, the mixture was extracted three times with a mixed solvent of H2O / EA, and the organic layer was washed with saturated sodium carbonate. The organic layerAfter drying with MgSO4, the solvent was concentrated under reduced pressure, and a silica gel column was carried out to obtain the title compound (475 mg, 83%)

The synthetic route of 706791-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YONSEI University Office of Research Affairs / University Industry Foundation; Korea Research Institute of Chemical Technology; Jang Seong-yeon; Lee Hyeok; Kim Seong-hwan; Kim Beom-tae; Kim Seong-su; Huh Jeong-nyeong; Im Hwan-jeong; Im Seung-gil; Kang Myeong-mo; Noh Gyeong-tae; Lee Gyeong-ro; Choi Ji-won; (147 pag.)KR2017/94087; (2017); A;,
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Electric Literature of 35179-98-7, 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. 35179-98-7, name is Chloromethyl ethyl carbonate, This compound has unique chemical properties. The synthetic route is as follows.

234 mg of (R) -2-chloro-1- (1-phenethyl) -1H-imidazole-5-carboxylic acid (CAS: 2093287-74-0) was dissolved in 20 mL of DMF, and 138 mg of ethyl chloromethyl carbonate was added Then, 275 mg of potassium carbonate was added, and the mixture was stirred at room temperature for 3 hours. After the reaction solution was filtered, it was poured into 150 mL of water and extracted with 100 mL of dichloromethane. The organic layer was separated and dried over anhydrous sodium sulfate overnight. The filtrate was filtered the next day and concentrated under reduced pressure to give a yellow oil. Column chromatography 242 mg of colorless oil was obtained, yield: 72.0%.

The chemical industry reduces the impact on the environment during synthesis Chloromethyl ethyl carbonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chongqing Maidisheng Pharmaceutical Technology Co., Ltd.; Yang Liang; (35 pag.)CN110655490; (2020); A;,
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Synthetic Route of 6279-86-3, 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 6279-86-3 as follows.

Put 300 ml methylbenzene and 60% sodium hydride 3.3g (0.0825 mol) into the 500 ml four-neck flask with reflux condenser pipe, dropping pipette, stirrer and thermometric instrument which is protected by dry nitrogen; and then add 19.3g (0.083 mol) methane tricarboxylic acid triethyl ester into the flask at the temperature of below 80C and protected for 2h by heat preservation; add 33.3g (0.075 mol) bromine sulfonium salts into the flask and then raise the temperature and control the temperature of the entire flask at 80C for a 15h reaction; cool it to the normal temperature and use 5% sulfuric acid to adjust the pH to pH=3; separate the organic layer and extract the water layer by 100 ml methylbenzene for two times; use 40 ml 5% sodium bicarbonate water solution wash the organic layer for two times; dry the oil layer by anhydrous sodium sulfate, filtrate and reduce pressure to recycle faint yellow fluid, finally get the target object-2.5g tri-ester dibenzyl biotin (95.5% of the theoretical value), and the HPLC measured content is 97.8% with no impurity 5 (hereinafter to be referred as dicarboxylic ester)

According to the analysis of related databases, 6279-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Medicine Co., Ltd.; EP2433942; (2012); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

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; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Related Products of 52449-43-1, 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 52449-43-1 as follows.

Example 50AMethyl (4-chlorophenyl)(cyclopentyl)acetate; A suspension of 3.65 g (32.5 mmol) of potassium tert-butoxide in 65 ml of abs. DMF was cooled to 0 C., and a solution of 5.0 g (27.08 mmol) of methyl 4-chlorophenylacetate in about 2 ml of abs. DMF was added dropwise. The mixture was stirred at 0 C. for 30 min, and 4.84 g (32.5 mmol) of cyclopentyl bromide were then slowly added dropwise. The reaction mixture was stirred at 0 C. for 1 h and then added to water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1). This gave 6.28 g of the target compound (91.8% of theory).GC-MS (Method 1): Rt=6.07 min; m/z=193 (M-C2H3O2)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.96-1.04 (m, 1H), 1.08-1.37 (m, 2H), 1.37-1.48 (m, 1H), 1.49-1.70 (m, 3H), 1.79 (dtd, 1H), 2.33-2.50 (m, 1H), 3.42 (d, 1H), 3.58 (s, 3H), 7.29-7.46 (m, 4H).

According to the analysis of related databases, 52449-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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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 40258-78-4 as follows. Safety of 1-Bromoethyl acetate

[5-(6-Chloro-5-cyano-1-methansulfonyl-1H-indol-2-yl)-6-(2-methoxyethoxymethoxy)biphenyl-3-yloxylacetic acid ethyl ester 260A mixture of 6-chloro-2-[5-hydroxy-2-(2-methoxyethoxymethoxy)biphenyl-3-yl]-1-methansulfonyl-1H-indole-5-carbonitrile (7.0 g, 13 mmoles) and K2CO3 (5.5 g, 23 mmoles) in acetonitrile (200 ml), was mixed with NaI (0.5 g) and bromoethyl acetate (1.6 ml, 14 mmoles). The mixture was stirred for about 18 h at ambient temperature, concentrated, the residue was dissolved in ethyl acetate (400 ml) and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated to afford 8.0 g (98percent) of the title compound as a brown foam.

According to the analysis of related databases, 40258-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Axys Pharmaceuticals, Inc.; US6867200; (2005); B1;,
Ester – Wikipedia,
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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. 4519-46-4, name is Methyl 2-bromoacrylate, A new synthetic method of this compound is introduced below., Formula: C4H5BrO2

EXAMPLE 5 2-Benzyloxycarbonyl-7-bromo-7-methoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene To 40 g. (0.2 moles) of N-benzyloxycarbonyl-1,2-dihydropyridine prepared as described in Example 3, 38 g. (0.23 moles) of freshly prepared methyl alpha-bromoacrylate and 2 g. of hydroquinone are added. The reaction mixture is allowed to stand at room temperature for 48 hours, under protection from light. The completion of the cycloaddition is shown by the disappearance of the lambdamax =305 nm from the UV spectrum. The reaction mixture is evaporated to an oily residue in vacuo, on a water bath of 40-50 C., and extracted from three 40-ml. portions of a benzene/brine mixture. The benzene phase is dried over magnesium sulfate and evaporated in vacuo, whereupon it is column chromatographed on a 30-fold amount of Kieselgel (0.063-0.2 mm), using a 10:1 mixture of benzene and ethyl acetate for the elution. Yield: 8 g. (0.01 moles), 11% based on the starting pyridine

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; Richter Gedeon Vegyeszeti Gyar Rt.; US4563464; (1986); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics