Category: esters-buliding-blocks

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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 3-bromobenzoate

Ethyl 3-bromobenzoate (0.500 g, 2.18 mmol) was dissolved in CH3CN ( 8.70 ml). Triethylamine (1.53 ml, 10.9 mmol) was added followed by 3,3-dimethylbut-l-yne (0.27 g, 3.27 mmol). With stirring Pd(PPh3)4 (0.25 g, 0.21 mmol) and CuI (0.083 g, 0.436 mmol) were added and the reaction was warmed to 60 C for 4 h. The reaction was then diluted with EtOAc (~ 50 ml), filtered through a pad of SiO2, and concentrated in vacuo. The crude product was purified on 40 g SiO2 using hexanes-EtOAc (10:1) as eluent giving 0.45 g of the title compound as a colourless oil (91 %); m/z 231.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/24834; (2006); 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. 126430-46-4, name is Benzyl 4-bromobutanoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

Step 2 4-(3-Benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-butyric Acid A mixture of 0.9 g of 4-bromobutyric acid benzyl ester, 0.5 g of 3-benzyl-8-aza-bicyclo[3.2.1]octane, 0.6 mL of N,N-diisopropylethylamine and 20 mL of acetonitrile was heated to 80 C. for 4 h. The mixture was cooled, concentrated under reduced pressure and partitioned between chloroform and saturated sodium carbonate. After drying over magnesium sulfate the extracts were concentrated to a thick oil, 1.4 g, which was a mixture of the benzyl ester of 4-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-butyric acid, benzyl 4-bromobutyrate, and butyrolactone. Hydrogenation over 0.5 g of palladium on carbon in 100 mL of ethanol under 1 atm of hydrogen overnight gave 0.9 g of 4-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-butyric acid after drying under vacuum at 100 C. overnight which was homogeneous by TLC (90:10:1 chloroform:methanol:ammonium hydroxide).

According to the analysis of related databases, 126430-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US6432976; (2002); B1;,
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. 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H9BrO2

At 0¡ãC, lithium aluminum hydride (1.425 g, 37.5 mmol) was dropped into a solution of methyl 4-bromo-2-methylbenzoate (5.725 g, 25 mmol) in tetrahydrofuran (120 mL) slowly. The ice-salt bath used was removed after that dropping. The reaction was complete (detected by LCMS and TLC) after stirred for 1 hour at room temperature. The mixture was cooled to 0¡ãC again and the reaction was quenched with water (1.43 mL) and 10percent NaOH solution (14.3 mL) respectively. After stirred for 15 min at room temperature, the mixture was filtered and then the filter cake was washed with tetrahydrofuran (80 mL*2) and ethyl acetate EA (80 mL*2). The filtrate was dried with anhydrous sodium sulfate, filtered, and then concentrated to obtain a colorless oil product (4.535 g, 90percent yield).

The synthetic route of 99548-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUZHOU CONNECT BIOPHARMACEUTICALS, LTD.; ZHENG, Wei; PAN, Wubin; YANG, Xin; (47 pag.)EP3048103; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, 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 57486-67-6, HPLC of Formula: C9H9FO2

A solution of methyl 2-(2- fluorophenyl)acetate (6.373 g, 37.89 mmol) and methyl iodide (5.90 mL, 94.8 mmol, 2.5 equiv) in anhydrous THF (25 mL) was treated portionwise with sodium hydride (60% suspension in mineral oil, 3.32 g, 83.0 mmol, 2.2 equiv) at 0 C, warmed to room temperature and reacted for 24 h. The reaction mixture was transferred into a separatory funnel with ice/water and acidified with 1.0 M HC1 (30 mL). The product was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed brine, filtered through cotton, and concentrated under reduced pressure to yield light yellow oil. The oil was dissolved in 16 mL of l,4-dioxane and 19.0 mL of 6.0 M NaOH (113.7 mmol, 3.0 equiv) was added. The mixture was heated at 95 C for 24 h. 30 mL of 3.0 M HC1 was added and the mixture was extracted with dichloromethane (3 x 20 mL). Combined organic fractions were washed with brine (30 mL), filtered through cotton and concentrated under reduced pressure to yield a crude mixture which was purified by flash chromatography (hexanes/ethyl acetate), 5.799 g of 2-methyl-2-(2-fluorophenyl)propanoic acid (31.83 mmol, 84% over two steps).

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; UNIVERSITY OF HOUSTON SYSTEM; DUBROVSKIY, Anton; KRIVOSHEIN, Arcadius, V.; (41 pag.)WO2019/99760; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 57381-62-1, 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. 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-bromo-4-chlorobenzoate (In-27, 5.0 g, 20.0 mmol) in MeOH (50 mL) was added N2H4.H20 (80percent, 50 mL). The resulting solution was heated at 60 ¡ãC for 1 h, until TLC show SM consumed. After concentration, the resulting solid was dissolved in EA (100 mL), washed with brine (2 x 30 mL), dried over Na2504 and concentrated to dryness to afford desired product 2-bromo-4-chlorobenzohydrazide Sc (2.8 g, 56percent). ?H NMR(300 MHz, DMSO-d6): oe 9.58 (s, 1H), 7.80 (d, J=1.8 Hz, 1H), 7.52 (dd, J8.1 Hz, J=2.1 Hz, 1H), 7.38 (d,J=8.1 Hz, 1H), 4.49 (s, 2H). LC-MS [M+Hj 251;

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; HAJJAR, Roger; DEVITA, Robert; (68 pag.)WO2019/18718; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 40876-98-0, 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. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of lH-pyrazol-3-amine (45 g, 542.16 mmol) in acetic acid (297 mL) and water (900 mL) was cooled to 0 C and diethyl oxaloacetate sodium salt (113.85 g, 542.16 mmol) was added. The resulting solution was heated at 100 C for 16 h. After which time the solids were filtered and dried to obtain the title compound (22% yield).

The synthetic route of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, W.; CAMPBELL, John, Emmerson; WO2014/100665; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27798-60-3, name is Methyl 2-Methoxyphenylacetate, 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 27798-60-3, Application In Synthesis of Methyl 2-Methoxyphenylacetate

General procedure: The methyl arylacetate (1 equiv.) and p-ABSA (1.3 equiv.) were dissolved in acetonitrile and cooled to 0 C using an ice bath under an argon atmosphere. 1,8-Diazabicycloundec-7-ene (DBU, 1.3 equiv.) was then added to the stirring mixture over the course of 5 minutes. After the addition of the DBU, the reaction mixture continued to stir at 0 C for an additional 15 minutes. Once this allotted time had passed, the ice bath was removed and the reaction mixture was stirred for 24 hours at room temperature. The resulting orange solution was quenched with saturated NH4Cl and the aqueous layer was extracted with diethyl ether (3x). The organic layer was then washed with deionized H2O to remove any residual salts. The combined organic layers were dried over MgSO4 and filtered. The organic layer was then concentrated under reduced pressure. The residue was purified via flash chromatography on silica gel (10:1 Hexanes:EtOAc).

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:
Article; Chepiga, Kathryn M.; Qin, Changming; Alford, Joshua S.; Chennamadhavuni, Spandan; Gregg, Timothy M.; Olson, Jeremy P.; Davies, Huw M.L.; Tetrahedron; vol. 69; 27-28; (2013); p. 5765 – 5771;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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 56741-34-5, Quality Control of Methyl 5-amino-2-fluorobenzoate

Step C : Methyl 5-amino-2-fluorobenzoate (5.21g, 30. 8MMOL) was added to a solution of concentrated sulfuric acid (45mL) in water (110ML). The resulting mixture was heated at 80C for 20min then cooled to 0C and treated dropwise with a solution of NaNO2 (2.34g, 33. 9MMOL) in lOmL of water. After stirring for 30MIN, a solution OF KI (7.16g, 43. 1MMOL) in 20mL of water was added. The reaction mixture was then warmed to rt and stirred overnight under a nitrogen atmosphere. Then the reaction mixture was stirred at 70C for 15MIN, cooled to rt, and extracted twice with ether. The combined ethereal layers were washed four times with water, once with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, 10% ethyl ACETATE/HEXANES) provided methyl 2-FLUORO-5-IODOBENZOATE. LH NMR (500 MHz, CDC13) 8 8.25 (dd, 1H), 7.82 (M, 1H), 6.94 (dd, IH), 3.95 (s, 3H). ESI-MS calc. for C8H6FI02 : 280; Found: 281 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2004/92124; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 35180-01-9,Some common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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.

In 1000 ml reaction flask by adding 400 ml acetonitrile, 50mlNMP and 40g tynofovir a water composition, stirring is opened, to control the temperature to 20 C dropping under 67g triethylamine, drops to continue dropping 100g chloro methyl isopropyl carbonate, the reaction system after the dipping temperature is increased to 50 C insulation reaction 8 hours, the detection reaction monoester less than 10%, in the reaction liquid 40 C the following concentrate under reduced pressure until there is no liquid can flow out, in the concentrated residual liquid by adding 500 ml ethyl acetate, 200ml6% of sodium bicarbonate solution, stir layered after extraction, the organic phase continue to use 200 ml purified water washing two times, the resulting organic phase after drying by anhydrous sodium sulfate concentrated under reduced pressure to dry, the resulting concentrated residual liquid directly used for the next reaction.

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Homesun Pharmaceutical Co., Ltd.; Fan, Chao; (7 pag.)CN105418684; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15964-79-1, 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 15964-79-1 as follows.

1-Isopropyl-6,7-dimethoxyisoquinolin-3-ol SIL 32164 To a solution of methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 (10.09 g, 48.0 mmol) in isobutyric anhydride (60.5 mL, 364.8 mmol) at 0 C. in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added HClO4 (ca. 70% solution in water, 4.91 mL, 56.8 mmol) over a period of 10 min. The reaction mixture was then allowed to warm up to RT, stirred for 2 h and diluted with Et2O (400 mL). The solid was filtered and washed several times with Et2O to give 16.88 g of a brown solid. The solid was then suspended in H2O (70 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer and cooled in an ice bath before dropwise addition of concentrated NH4OH (180 mL). After complete addition, the ice bath was removed and the reaction mixture was stirred overnight at RT. The mixture was then extracted with CH2Cl2 (100 mL, the organic layer was isolated and the aqueous layer was further extracted with CH2Cl2 (3*100 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum to give 1-isopropyl-6,7-dimethoxyisoquinolin-3-ol SIL 32164 as a yellow solid (9.69 g, 82% yield). MW: 247.29; Yield: 82%; Yellow solid; Mp ( C.): 175.0 1H-NMR (CDCl3, delta): 1.52 (d, 6H, J=6.9 Hz, 2*CH3), 3.63-3.70 (m, 1H, CH), 3.93 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 6.57 (s, 1H, ArH), 6.60 (s, 1H, ArH), 6.94 (s, 1H, ArH), OH not seen. 13C-NMR (CDCl3, delta): 21.1 (2*C), 29.4, 55.8, 56.0, 101.8, 102.8, 104.8, 111.8, 142.0, 147.5, 154.5, 154.8, 161.2. MS-ESI m/z (% rel. Int.): 248 ([MH]+, 100).

According to the analysis of related databases, 15964-79-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ExonHit Therapeutics SA; ALLERGAN, INC.; US2012/214837; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics