Category: esters-buliding-blocks

Reference of 39149-80-9, 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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

yl)propanoate (R)-6-chloro-4-(3-methylpiperazin-1-yl)pyridazin-3-amine (370 mg, 1.62 mmol) (prepared as in example G02939250) was dissolved in dimethylformamide (8 mL) for the addition of tert-butyl 2-bromopropanoate (0.44 g, 2.11 mmol), followed by potassium carbonate (0.45 g, 3.24 mrnol). The solution was heated to 60 C for 72 h. The reaction mixture waspartitioned between ethyl acetate and sodium bicarbonate (aq., sat.). The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluting with hexanes and ethyl acetate) to afford the title compound (0.42 g, 1.19 mmol, 73%). LCMS I41Z (M+H) 356.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-bromopropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, 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 18595-14-7, Computed Properties of C9H11NO2

An autoclave was charged with a mixture of methyl 4-amino-3-methylbenzoate (10.0 g, 60.5 mmol, Cas No18595-14-7), rhodium 5% on charcoal (3.74 g, 50% wet), acitic acid (5.2 ml)and ethanol (100 ml) and pressurized with hydrogen (12 bar). The mixture was stirred at 80C for 22 h. For work-up, the catalyst was filtrate d off, washed with ethanol and the filtratewas concentrated under reduced pressure. The residue was dissolved in dichloromethane(250 ml) and hydrochloric acid (30 ml, 120 mmol, 4 M in dioxane) was added. The mixturewas concentrated und reduced pressure and the residue was codestilled with toluene (2x) togive the crude product as a mixture of isomers which was used without further purification.

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 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Synthetic Route of 18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 250 mL round bottom flask was charged with diethyl 2,5-dibromo-terephthalate (9.12 g, 24 mmol), 2-tri-n-butyltin-thieno[3,2-b]thiophene (25.76 g, 60 mmol) and tetratriphenylphosphine palladium (277.3 Mg, 0.24mmol). Nitrogen gas was purged three times, and toluene (120 mL) except oxygen was added, and the mixture was refluxed under nitrogen for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and dichloromethane was evaporated. The mixture was separated by silica gel column chromatography using dichloromethane as eluent to give diethyl 2,5-bis(thieno[3,2-b]thiophen-2-yl)terephthalate (8.98 g, yield 75%).

The synthetic route of Diethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Ningbo Materials Technology And Engineering Institute; Fang Junfeng; Zhang Wenjun; Song Changjian; (26 pag.)CN109232604; (2019); A;,
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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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H18O4

12.6 g of sodium hydride (purity: 60%, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10C, 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100%) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t)

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 10601-80-6.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1364946; (2003); A1;,
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Synthetic Route of 680217-71-4, 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 680217-71-4 as follows.

A mixture of scheme 27 compound 4 (1.4 g, 7.07 mmol) and (2,6-difluoro-phenyl)-acetic acid ethyl ester (2.63 g, 14.14 mmol), CS2CO3 (6.9 g, 21.2 mmol), were dissolved in DMF. The reaction mixture was heated to 110 C and stirred for 4h. The mixture was evaporated in vacuo, the residue was purified by silica gel column chromatography (DCM/MeOH = 100/1 to 10/1) to give the scheme 27 compound 5 (410 mg, 17%) as a yellow solid.

According to the analysis of related databases, 680217-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
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Some common heterocyclic compound, 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, molecular formula is C6H10O3, 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. HPLC of Formula: C6H10O3

Triphenylphosphine (0.948 g, 3.61 mmol) was added to a solution of 4-methyl-/V- (quinolin-8-yl)benzenesulfonamide (Intermediate 88A) (1 .08 g, 3.61 mmol) in tetrahydrofuran (30 ml_). The reaction mixture was cooled to 0 C, and methyl 3- hydroxycyclobutanecarboxylate (0.35 ml_, 3.0 mmol) was added, followed by DIAD (0.70 ml_, 3.6 mmol). The reaction mixture was then warmed to room temperature, stirred overnight, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organics were washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc- hexanes gradient to give the title compound (0.691 g, 56%). 1H NMR (400 MHz, CD3SOCD3) delta 1 .79-1 .93 (m, 1 H), 2.04 (dt, J = 8, 4 Hz, 1 H), 2.25-2.36 (m, 1 H), 2.36-2.46 (m, 4 H), 2.66- 2.76 (m, 1 H), 3.60 (s, 3 H), 4.97 (t, J = 8 Hz, 1 H), 7.32 (d, J = 8 Hz, 2 H), 7.49-7.59 (m, 4 H), 7.65 (t, J = 8 Hz, 1 H), 8.06 (dd, J = 8, 1 Hz, 1 H), 8.41 (dd, J = 8, 1 Hz, 1 H), 8.71 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 41 1 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 63485-50-7, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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These common heterocyclic compound, 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, 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. Safety of Ethyl 4,4-difluorocyclohexanecarboxylate

Step 5 4,4-Difluoro-cyclohexanecarboxylic acid: A solution of 4,4-difluoro-cyclohexanecarboxylic acid ethyl ester (970 mg, 5.0 mmol) in ethanol (5 mL) was treated with 2N sodium hydroxide (3.8 mL, 7.6 mmol) at 0 C., and the mixture was allowed to warm to ambient temperature and stirred for an additional 18 hours. The mixture was diluted with water (15 mL), and the pH was adjusted to 3-4 with 6 N hydrochloric acid. The mixture was extracted with toluene, dried and concentrated to give the title compound as a white solid. Yield: 758 mg (92%). 1H-NMR (CDCl3.) delta: 1.60-2.23 (m, 8H), 2.45 (m, 1H).

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

Reference:
Patent; Auspex Pharmaceuticals, Inc.; US2008/146605; (2008); 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. 541-16-2, name is Di-tert-Butyl malonate, A new synthetic method of this compound is introduced below., Safety of Di-tert-Butyl malonate

7a. Preparation of (1R,2R)/(1S2S) 1-amino-2-ethylcyclopropanecarboxylic Acid tert-butyl Ester (Racemic Mixture); Step 1: Preparation of 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester, Shown Below To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred for 18 hours at room temperature and treated with a mixture of ice and water. The crude product was extracted with dichloromethane (3*) and sequentially washed with water (3*), and brine. The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography (100 g SiO2, 3% diethyl ether in hexane) to provide the desired product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Ester – Wikipedia,
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Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2×20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
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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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H14ClNO2

Description 169: methyl 4-(1-(5-chloro-2-(3-((2,4- difluorophenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D169)A mixture of 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1 -yl)nicotinic acid (D1 18) (40 mg, 0.1 18 mmol), 1 -Hydroxybenzotriazole hydrate (18 mg, 0.1 18 mmol) and 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34 mg, 0.177 mmol) in dimethylformamide (5ml) was stirred 10 min at room temperature. A solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (32.2 mg, 0.141 mmol) and triethylamine (0.02ml, 0.141 mmol) in dry dimethylformamide (2ml) was added and the mixture was stirred 24h at room temperature. After solvent evaporation, water (10ml) was added and the formed precipitate was filtered off and purified by Biotage SNAP-Si (1 Og) cartridge eluting with a mixture dichloromethane/methanol from 100/0 to 80/20. Collected fractions, after solvent evaporation afforded the title compound (D169) (105 mg).MS: (ES/+) m/z: 513.2 [MH+] C26H23CIF2N403 requires 512.141 H NMR (400MHz ,DMSO-d6) delta = 9.23 (s, 1 H), 8.21 (d, J = 2.4 Hz, 1 H), 7.91 – 7.80 (m, J = 8.3 Hz, 2 H), 7.74 (d, J = 2.4 Hz, 1 H), 7.40 – 7.29 (m, J = 8.3 Hz, 2 H), 7.18 – 7.06 (m, 1 H), 6.85 (t, J = 8.6 Hz, 1 H), 6.48 (d, J = 5.4 Hz, 1 H), 6.03 (br. s., 1 H), 4.22 (d, J = 3.9 Hz, 3 H), 3.86 (s, 3 H), 3.76 (d, J = 4.9 Hz, 2 H), 1 .34 (d, J = 9.3 Hz, 4 H)

According to the analysis of related databases, 1014645-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
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