Month: February 2021

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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 3-(dimethylamino)acrylate

Step c) 3-(4-Chloro-phenyl)-isoxazole-4-carboxylic acid ethyl ester To a solution of (E)- and/or (Z)-N-hydroxy-4-chloro-benzenecarboximidoyl chloride (58.0 g, 250.3 mmol) in diethylether (1.04 L) was added a solution of ethyl 3-(N,N-dimethylamino)acrylate (90.4 mL, 624 mmol) and triethylamine (50.1 mL, 362 mmol) in diethylether (1.04 L). The resulting mixture was then stirred for 14 h at room temperature and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title product (57 g, 91%) which was obtained as a white solid. MS: m/e=252.1 [M+H]+.

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; Hoffmann-La Roche Inc.; Dott, Pascal; Hanlon, Steven Paul; Hildbrand, Stefan; Iding, Hans; Thomas, Andrew; Waldmeier, Pius; US2013/102778; (2013); A1;,
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Application of 59247-47-1,Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1 ,2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.l]heptane ll3h (150 rng, 0.42 mmol, l.O equiv.), Tol (20 rnL),tert-butyl4-bromobenzoate (161.2 mg, 0.63 mmoL 1.50 equiv.), Cs2C03 (408 8 mg, 1.25mmol, 3.0 equiv.), BIANP (13 mg), and Pd2(dha)3 (19 mg, 0.02 mmol, 0.05 equiv.). The5 resulting mixture was stirred at 110 ¡ãC overnight Solids were filtered out. l11e illtrate wasconcentrated under vacuum to a residue which was pmified by silica gel columnchromatography eluting with ethyl acetate/petroleum ether (l: 10 to 1 :5). Removal of solventsgave tert-huty 1 4-l(l S,4S,5R)-5-U 3-(2-chloro-6-methy lpheny 1)-5-cyclopropy 1-1,2-oxazol-4-y l] rnethoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]henzoate ll4a (l 00 mg, 45percent) as a light yellow10 oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10047-10-6, name is Methyl 2-aminopentanoate hydrochloride, 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 10047-10-6, category: esters-buliding-blocks

General procedure: To a solution of N-chlorosulfonyl isocyanate (11.32 g; 80 mmol) in dry methylene chloride (120 mL) cooled in an ice bath was added dropwise a solution of t-butyl alcohol (5.93 g; 80 mmol) in dry methylene chloride (120 mL). The resulting mixture was added dropwise to a mixture of glycine methyl ester hydrochloride (10.05 g; 80 mmol) and triethylamine (16.16 g; 160 mmol) in dry methylene chloride (120 mL) kept at 0 C. The ice bath was removed and the reaction mixture was allowed to stir at room temperature overnight. The resulting solution was washed sequentially with 5% aqueous HCl (3 ¡Á 100 mL) and brine (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and the solvent was removed on the rotary evaporator, leaving compound 1a as a white solid (14.56 g; 68% yield), mp 98-100 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:
Article; Dou, Dengfeng; Tiew, Kok-Chuan; Mandadapu, Sivakoteswara Rao; Gunnam, Mallikarjuna Reddy; Alliston, Kevin R.; Kim, Yunjeong; Chang, Kyeong-Ok; Groutas, William C.; Bioorganic and Medicinal Chemistry; vol. 20; 6; (2012); p. 2111 – 2118;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18595-18-1, 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ammonium thiocyanate (50 mmol) is dissolved in 50 ml of acetone, 40 C lower dropwise acetyl chloride (50 mmol) in 10 ml acetone solution, stirring 1 hour, then cooling to room temperature, is slowly added 3-amino-4-methyl benzoic acid methyl ester in 75 ml of acetone solution, stirring the mixture at room temperature for 5 hours, adding 100 ml of water, is continuously stirred for 1 hour, filtering the precipitation separated out, water washing 3 times, hexane washing 3 times, vacuum drying to obtain title compound 11.3 g. 1 H-NMR (DMSO), delta 12.19 (1H, s), 11.56 (1H, s), 8.18 (1H, s), 7.77 (1H, d, J=8.0Hz), 7.45 (1H, d, J=8.0Hz), 3.84 (3H, s), 2.27 (3H, s), 2.17 (3H, s).

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

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICALGROUP CO LTD; Beijing Centaurus Biopharma Technology?Co.,?Ltd.; XIAO, DENGMING; LIANG, ZHI; HU, YUANDONG; HU, QUAN; ZHANG, QINGHUI; HAN, YONGXIN; WANG, HUAN; PENG, YONG; KONG, FANSHENG; LUO, HONG; (60 pag.)CN103130792; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61644-18-6, A common heterocyclic compound, 61644-18-6, name is Chloromethyl isobutyrate, molecular formula is C5H9ClO2, 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.

EXAMPLE 6 Preparation of isobutyryloxymethyl trans-4-aminomethylcyclohexanecarboxylate (Method A) Sodium bromide (3.8 g; 0.037 mol and isobutyryloxymethyl chloride (5.1 g; 0.037 mol) was mixed with dimethylformamide (40 ml) and stirred for 3 h at room temperature. Trans-4-(tert.-butoxycarbonylaminomethyl)cyclohexane carboxylic acid (15.4 g; 0.06 mol) dissolved in dimethylformamide (100 ml) and triethylamine (12 g; 0.12 mol) was added and the stirring continued for 100 h at room temperature. The solvent was evaporated and water and diethylether were added. The ether layer was washed, dried and evaporated to give 6.1 g. This product was dissolved in ethyl acetate and ethyl acetate/hydrochloric acid was added. After 3 h at room temperature ether was added and the precipitate collected. Yield 3.5 g., m.p. 100 C. The product was dissolved in chloroform. Some undissolved material was filtered off and the solution was evaporated. M.p. 104 C. Calculated for: C13 H24 Cl NO4: C 53.2, H 8.23, N 4.77, O 21.8, Cl 12.1, found: 53.5, 7.78, 4.65, 21.2, 12.1.

The synthetic route of 61644-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KabiVitrum AB; US4483867; (1984); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 474709-71-2, name is Ethyl 4-bromo-2-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 4-bromo-2-fluorobenzoate

EXAMPLE 73 4-Bromo-2-ethoxy-benzoic acid ethyl ester Sodium (1.815 g, 78.9 mmol, Aldrich) was cut into small pieces and added to ethanol (100 mL). After all the pieces were dissolved, the clear solution was added to a solution of ethyl 4-bromo-2-fluoro-benzoate (13 g, 52.6 mmol) in ethanol (20 mL) cooled to 0 C. The ice bath was then removed and the mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated in vacuo, and the residue was taken in water and 20% ethyl acetate-hexane. The organic layer was washed with saturated solution of sodium bicarbonate, brine, and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (120 g of silica gel, eluding with 10-15% ethyl acetate in hexane) gave 4-bromo-2-ethoxy-benzoic acid ethyl ester as white solids (11.020 g, 77%).

The synthetic route of 474709-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ding, Qingjie; Graves, Bradford James; Kong, Norman; Liu, Jin-Jun; Lovey, Allen John; Pizzolato, Giacomo; Roberts, John Lawson; So, Sung-Sau; Vu, Binh Thanh; Wovkulich, Peter Michael; US2007/129416; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 185629-32-7 as follows. name: Methyl 4-amino-3-fluorobenzoate

Example 79A Methyl 4-{[(6-bromo-5-chloro-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-fluorobenzoate (0654) (0655) To a solution of 357 mg (0.84 mmol) of the compound from example 78A and 156 mg (0.92 mmol) of 158 methyl 4-amino-3-fluorobenzoate in 1.0 ml of 49 DMF under argon was added 0.84 ml (0.84 mmol) of a 1 M solution of 153 potassium tert-butoxide in 163 THF. The mixture was stirred at RT for 2.5 h. Subsequently, another 0.84 ml (0.84 mmol) of a 1 M solution of potassium tert-butoxide in THF was added, and stirring of the mixture was continued at RT overnight. Thereafter, the mixture was admixed with 30 ml of 10% 83 aqueous citric acid solution and 30 ml of 43 water. The precipitate formed was filtered off, washed twice with 10 ml of water and dried under reduced pressure. 289 mg of a 283 product batch were obtained, in which the title compound, by LC/MS analysis, was present in 4% purity (3% of theory). This material was used in subsequent reactions without further purification. (0656) LC/MS (Method 23, ESIpos): Rt=4.16 min, m/z=527/529 [M+H]+.

According to the analysis of related databases, 185629-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 369-25-5, 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. 369-25-5 name is Methyl 3,4-difluorobenzoate, 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 4-bromo-3-(1,3-dioxolan-2-yl)phenol (7.1 g, 29 mmol, 1 eq), methyl 3,4-difluorobenzorate (5 g, 29 mmol, 1 eq), potassium carbonate (6 g, 43.5 mmol, 1.5 eq) in DMF (29 mL). Reaction was stirred at 100 C. over night. TLC showed that reaction was completed. After cooling to room temperature, the residue was removed by filtration. The residue was washed with EtOAc. The organics were combined and concentrated via Rota vapor. The residue was poured into EtOAc and water. The organic layers was separated and washed with brine and dried over sodium sulfate anhydrous. Filter and concentrated to get methyl 4-(4-bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-fluorobenzoate as crude, light brown oil, which was used for next step without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,4-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 618-89-3, The chemical industry reduces the impact on the environment during synthesis 618-89-3, name is Methyl 3-bromobenzoate, I believe this compound will play a more active role in future production and life.

a. 3-Morpholin-4-yl-benzoic Acid Methyl Ester Following the procedure above except substituting “morpholine” for “pyrrolidine” and “methyl-3-bromobenzoate” for “methyl-4-bromobenzoate” gave the title compound: MS (M+H+): 222.

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

Reference:
Patent; Quibell, Martin; Taylor, Steven; Grabowska, Urszula; Nilsson, Magnus; Morrison, Veronique; US2003/186962; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 13195-64-7, 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. 13195-64-7, name is Diisopropyl malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The catalyst 10a/10b (0.01 mmol) and aldehyde 1(0.1 mmol) were dissolved in ethanol (2.0 mL). The reactionmixture was stirred for about 10 min, and then malonate2 (1.0 mmol) and triethylamine (0.2 mmol) were added atroom temperature. After vigorous stirring for about 48-72 h,the reaction mixture was poured into water (3 mL) andextracted with ethyl acetate (3 ¡Á 15 mL). The organic fractionwas dried over anhydrous MgSO4and concentratedunder reduced pressure. The crude product was purified bycolumn chromatography to afford 3a-p as desired products.

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, Diisopropyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ashokkumar, Veeramanoharan; Siva, Ayyanar; Sankar, Balakrishnan; Journal of the Iranian Chemical Society; vol. 16; 9; (2019); p. 1939 – 1955;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics