Month: August 2021

Electric Literature of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 solution of 5-bromo-2-(phenylcarbonyl)-1 ,2-dihydro-1 -isoquinolinecarbonitrile (D10; 70 g, 206 mmol) and 1 , 1 -dimethylethyl 3-bromopropanoate (Aldrich; 37.9 ml, 227 mmol) in dry, degassed DMF (250ml) was added dropwise over 40 mins to a suspension of sodium hydride (60%; 24.76 g, 619 mmol) in dry, degassed DMF (750ml) at -10 0C under nitrogen. The mixture was stirred at -10 0C for 10 mins, then allowed to warm to room temp over 3h. Water (1500ml) was cautiously added and the mixture extracted with ethyl acetate (3x500ml). The combined organic extracts were washed with brine (5x500ml) and dried (MgSO4). The solvent was evaporated to give a brown oil. The crude intermediate was dissolved in THF (700ml) and lithium hydroxide (24.71 g, 1032 mmol) in water (100 ml) (note: not all soluble) was added. The mixture was vigorously stirred for 3Oh, then stored in the fridge over the weekend. The mixture was partitioned between water (700ml) and ethyl acetate (3x500ml) and the combined organic extracts washed with brine (2x500ml) and dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography on silica eluting with 5-15% ethyl acetate in isohexane gave the title compound (48.2g) MS (ES) Ci6H18BrNO2 requires 336; found 336/338 [M+H]+.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/133136; (2009); A1;,
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. 454-31-9, name is Ethyl 2,2-difluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 454-31-9

Step 2 Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was placed in a 250 mL Erlenmeyer flask, and dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25% sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected, washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.; 1 H NMR (DMSO-d6) 8.0 (m, 3H), 7.3 (t, 1H), 6.9 (s, 1H), 6.5 (t, 1H), 3.9 (s, 3H).

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5756529; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (VI-6), obtained above (1.4 g) in methylene chloride (10 mL) was added TFA (5 mL). The mixture was stirred at RT for an hour. The volatiles were removed in vacuo to yield crude product (VI-7) as its TFA salt (1.6 g) as yellow oil, which was used for the next step without further purification. ESI m/z: 266 (M + H)+.

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, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; REGENERON PHARMACEUTICALS, INC.; HAN, Amy; OLSON, William; MURPHY J., Andrew; (393 pag.)WO2018/89373; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 618-89-3, name is Methyl 3-bromobenzoate, 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 618-89-3, SDS of cas: 618-89-3

3-(3-bromophenyl)-3-oxopropanenitrile: Acetonitrile (21.86 mL, 419 mmol) was added to a stirred suspension of 60% NaH (7.25 g, 181 mmol) in THF (150 mL). Then, methyl 3-bromobenzoate (30 g, 140 mmol) was added and the mixture was heated at 75C for 4 h. After cooling to room temperature, water followed by iN HC1 (200 mL) was added and the mixture was extracted with ethyl acetate (500 mL), washed with sat .NaHCO3 solution (200 mL), dried (Na2SO4), filtered andconcentrated to afford 3-(3-bromophenyl)-3-oxopropanenitrile (29 g, 129 mmol, 93% yield) as light yellow solid. ?H NMR (500 MHz, CDC13) oe 8.09 (t, J1 .7 Hz, 1H),7.90 – 7.86 (m, 1H), 7.83 (ddd, J8.0, 2.0, 1.1 Hz, 1H), 7.45 (t, J7.9 Hz, 1H), 4.08(s, 2H).

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; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D’ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F.; WO2015/126376; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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.

[0542] To a solution of 269-2 (14.4 g, 8 mmol) in EtOH (120 mL) was added acetic anhydride (9.0 g, 88 mmol). The mixture was allowed to stir at 50 °C for 2 h. The mixture was cooled to r.t., and neutralized with aqueous NaHC03 solution. The mixture was extracted with EA (3 x 60 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-3 (15.0 g. 84.1 percent). +ESI-MS:m/z 223.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-2-methoxybenzoate, its application will become more common.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 61367-07-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 2,4,6-trichloropyridine (2.22 g, 12.20 mmol), methyl trans-4-aminocyclohexanecarboxylate hydrochloride (2.6 g, 13.42 mmol) and cesium carbonate (6.74 g, 48.8 mmol) in DMF (30 mL) was stirred in a sealed tube at 150 C. After 5.5 hours, the crude was poured on water (30 mL) and EtOAc (30 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (hexanes/ethyl acetate 15% to 30% ethyl acetate) gave the title compound (1.02 g, 28%) as a yellow solid.LRMS (m/z): 303/305 (M+1)+.1 H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.24 (m, 4H), 1.6 (m, 2H), 2.11 (m, 2H), 2.31 (m, 1 H), 3.26 (m, 1 H), 3.69 (s, 3H), 4.32 (d, J = 7.3 Hz, 1 H), 6.34 (s, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 10268-71-0,Some common heterocyclic compound, 10268-71-0, name is Phenyl 2-methoxybenzoate, molecular formula is C14H12O3, 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.

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 2-Methoxy-benzoic acid phenyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Methoxy-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.53 g, 8.3 mmol) as yellow solid in 59% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Phenyl 2-methoxybenzoate, its application will become more common.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 5941-55-9, A common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, 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.

To a cooled (-10 C) solution of (E)-ethyl 3-ethoxyacrylate (1 g, 6.94 mmol) in water (4 mL) and dioxane (4 mL) was added N-bromosuccinamide (NBS, 1.36 g, 7.63 mmol). The reaction was warmed to room temperature and stirred for one hour, at which point 6-chloropyridazin-3-amine (0.899 g, 6.94 mmol) was added reaction mixture was heated 80C for one hour. The reaction was cooled to room temperature and quenched via the addition of water. The product was extracted with ethyl acetate and the combined organic layers were washed with saturated (aq.) sodium chloride, dried over sodium sulfate, filtered, concentrated and purified using automated chromatography to provide ethyl 6-chloroimidazo[l,2-b]pyridazine-3-carboxylate (1 g, 61 % yield). LC retention time 1.42 min [O]. MS (E+) m/z: 226 (MH+).

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 10601-80-6,Some common heterocyclic compound, 10601-80-6, name is Ethyl 3,3-diethoxypropionate, molecular formula is C9H18O4, 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: 2-aminopyridine 1a (47 mg, 0.5 mmol), ethyl 3,3-diethoxypropanoate 2 (285 mg, 1.5 mmol) and p-TsOH (8.6 mg, 10 mol %) were stirred in 2 mL of toluene for 6 h at 80 C. After completion of the reaction (monitored by TLC), the water (10 mL) was added. The aqueous solution was extracted with ethyl acetate (3×8 mL) and the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether/ethyl acetate = 2:1) to give a pure sample of 3a (Yellow crystal, 100 mg, 82%).

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

Reference:
Article; Liu, Wenjie; Wang, Shaohua; Zhan, Haiying; Li, Mingshan; Synlett; vol. 25; 10; (2014); p. 1478 – 1481;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 454-31-9, Product Details of 454-31-9

Step 2: Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione. Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl t-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

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; G.D. Searle & Co.; US5990148; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics