Month: July 2021

Some common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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. SDS of cas: 61367-07-5

To a stirred solution of 25 (Nicolaou et al, 2016) (100 mg, 250 pmol, 1.0 equiv) in dry DMF (2 mL) at 0 C were added HATU (285 mg, 750 pmol, 3.0 equiv) followed by Et3N (200 pL, 1.50 mmol, 6.0 equiv) and the resulting mixture was stirred for 5 min at the same temperature. A solution of 26 (59.0 mg, 370 pmol, 1.5 equiv) in dry DMF (0.5 mL) was then added and the stirring was continued for 18 h while allowing the temperature to slowly rise to 23 C. The reaction mixture was diluted with H20 (5 mL) and the resulting solution was extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with brine (5 mL), dried over Na SCL and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (silica gel, 10 50% EtOAc in hexanes) to furnish 27 (113 mg, 210 pmol, 84% yield) as a white amorphous solid. 27: Rf= 0.50 (silica gel, 50% EtOAc in hexanes); [OC]D =-3.6 (c= 1.0, CHC13); FT-IR (film) VmaX: 2936, 1735, 1687, 1663, 1540, 1492, 1368, 1220, 1154, 1130, 1040, 771, 732 cnT1. NMR: (CDC13, 600 MHz) d 8.02 (d, = 2.1Hz, 1H), 7.12-7.01 (m, 1H), 5.82 (dd, J = 11.6, 2.9 Hz, 1H), 4.14-3.84 (m, 2H), 3.67 (d, = 1.5 Hz, 3 H), 2.71 (s, 3 H), 2.35-2.20 (m, 2H), 2.15 (s, 2H), 2.15-2.11 (m, 3 H), 2.10-1.98 (m, 3 H), 1.62 (d, = 15.2 Hz, 2H), 1.44 (s, 9H), 1.37- 1.22 (m, 3 H), 0.98-0.96 (m, 3 H), 0.86 (ap. d, J= 2.9 Hz, 3 H) ppm; 13C NMR: (CDC13, 150 MHz) d 175.7, 170.4, 160.0, 150.1, 139.7, 128.2, 123.3, 79.4, 69.2, 56.4, 51.6, 48.4, 47.7, 42.4, 35.0, 32.1, 31.9, 30.4, 28.3, 27.8, 20.9, 20.0, 19.5; Diagnostic signals of minor rotamer. 13C NMR: (CDCI3, 150 MHz) d 175.6, 170.1, 156.3, 150.3, 142.4, 131.0, 123.1, 79.8, 70.9, 51.6, 47.4, 42.3, 35.4, 32.0, 31.7, 30.5, 28.4, 27.8, 21.0, 19.7 ppm; HRMS calcd for C26H4iN307SNa+ [M+Na]+ 562.2563 found 562.2572.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61367-07-5, its application will become more common.

Reference:
Patent; WILLIAM MARCH RICE UNIVERSITY; NICOLAOU, Kyriacos, C.; ERANDE, Rohan, Diliprao; VOURLOUMIS, Dionisios; PULUKURI, Kiran, Kumar; RIGOL, Stephan; (262 pag.)WO2019/108685; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4341-76-8, 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. 4341-76-8, name is Ethyl 2-butynoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 2-aminopyridine (0.1mmol), alkynoate (0.1mmol) and AgSO3CF3 (30mol%) in chlorobenzene (0.8mL) was stirred at 120C for 24h. After the reaction was finished, water (5mL) was added and the solution was extracted with ethyl acetate (3×5mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.

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

Reference:
Article; Chen, Zhengwang; Wen, Yuelu; Ding, Hao; Luo, Guotian; Ye, Min; Liu, Liangxian; Xue, Jun; Tetrahedron Letters; vol. 58; 1; (2017); p. 13 – 16;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 18595-17-0, A common heterocyclic compound, 18595-17-0, name is Methyl 2-amino-4-methylbenzoate, molecular formula is C9H11NO2, 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.

REFERENCE EXAMPLE 25 Methanesulphonyl chloride (12.2 ml) was added to a stirred, cooled solution of methyl 2-amino-4-methylbenzoate (103 g) and triethylamine (19.5 ml) in dichlorotuethane while maintaining the temperatare below 0 C. The mixture was stirred at room temperature for 4 hours. Hydrochloric acid solution (2M) was added and the layers were separated. The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give a mixture of methyl 4-methyl-2-[N,N-bis(methylsulphonyl)amino]benzoate and methyl 4-methyl-2-(N-methylsulphonylamino)benzoate (18.26 g) as a yellow solid which was not further purified.

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; Rhone-Poulenc Argriculture Limited; US5658858; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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. Quality Control of Methyl 4-amino-2-methoxybenzoate

Example 286; Preparation of rac 4-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-2-methoxy-benzoic acid methyl ester To a stirred solution of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (100 mg, 0.17 mmol) in methylene chloride (10 mL), HATU (Aldrich,118 mg, 0.31 mmol) was added followed by the addition of DIPEA(0.15 mL, 0.86 mmol) and 4-amino-2-methoxy-benzoic acid (Avocado, 62 mg, 0.34 mmol). The mixture was stirred at rt for overnight. The reaction was quenched with addition of water. The mixture was extracted with methylene chloride (2.x.10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on an ISCO machine (40 g column, 5-15percent EtOAc/methylene chloride) to give a white solid. 29 mg.MS (ES+) m/z Calcd: [(M+H)+]: 630.1733, found: 630.1732

The synthetic route of Methyl 4-amino-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Liu, Jin-Jun; Ross, Tina Morgan; Zhang, Jing; Zhang, Zhuming; US2010/75948; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 22515-16-8, A common heterocyclic compound, 22515-16-8, name is Diethyl 4,4-difluoroheptanedioate, molecular formula is C11H18F2O4, 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.

A solution of diester (5.00 g, 19.8 mmol) in ethanol was cooled to 0 C; a solution of KOH (1 .22 g, 21 .8 mmol) in ethanol was added slowly to the reaction mixture. The resulting solution was warmed to rt and stirred for 10 h. The reaction mixture was coned, diluted with water, and extracted with hexanes:EA (3: 1 ). Tire aq phase was acidified with IN HC1 and extracted by EA. Tire organic phases were combined and dried over NarSOr, filtered, and coned to afford 2.88 g of the title compd as a white solid (65% yield). LCMS (ESI+): m/z = 225.21 | M 1 1 [ .

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; PLIANT THERAPEUTICS, INC.; LEFTHERIS, Katerina; REILLY, Maureen; FINKELSTEIN, Darren; COOPER, Nicole; BAILEY, Christopher; CHA, Jacob; (0 pag.)WO2020/6315; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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: Amines 10a-f (1.0 equiv), N,N-diisopropylethylamine (1.5 equiv), ethyl (E)-4-bromobut-2-enoate(5, 1.3 equiv) and CH2Cl2 (25 mL) were placed in a round bottom flask and stirred at 20 C for1 h, under nitrogen. After completion of the reaction (TLC) the reaction mixture was extracted withNaHCO3 (3 30 mL) and water (1 30 mL). The organic phase was dried over Na2SO4 and thesolvent removed under reduced pressure to yield the crude product. The crude product was purifiedby silica gel column chromatography (9:1 hexanes:EtOAc).Ethyl (E)-4-(thiazolidin-3-yl)but-2-enoate (14a). 1.21 g (63 %) as a yellow oil.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rodriguez-Lozada, Josue; Tovar-Gudino, Erika; Guevara-Salazar, Juan Alberto; Razo-Hernandez, Rodrigo Said; Santiago, Angel; Pastor, Nina; Fernandez-Zertuche, Mario; Molecules; vol. 23; 11; (2018);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 69812-51-7, The chemical industry reduces the impact on the environment during synthesis 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, I believe this compound will play a more active role in future production and life.

General procedure: To an oven-dried Schlenk tube equipped with a magnetic stir bar was charged with tris(2,2′-bipyridyl)ruthenium(II) chloride (3 mol%), arenesulfonyl chloride (1.0 equiv.), heteroarene (1.0 equiv.), Na2CO3 (1.0 equiv.) and dry acetonitrile. The mixture was degassed by the freeze pump-thaw procedure, and then the Schlenk tube was irradiated under a 3W Blue LED bulb at a distance of 5 cm. After stirring at 25 C for 12 h, the solvent was removed under reduced pressure and the residue was then diluted with water. The aqueous solution was extracted (3 times) with ethyl acetate. The combined organic phases were dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure to get the crude product, which was purified by column chromatography using hexane-ethyl acetate mixtures.

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

Reference:
Article; Natarajan, Palani; Bala, Anu; Mehta; Bhasin; Tetrahedron; vol. 72; 19; (2016); p. 2521 – 2526;,
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. 183322-16-9, name is Ethyl 3,4-bis(2-methoxyethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester (15.00 g, 0.05 mol) was added into acetic acid (50 ml) to form a mixture, and while the mixture was stirred in an ice water bath, 65%-68% nitric acid (13 ml) was added to the mixture. The mixture then was stirred for 24 h at room temperature. The reaction mixture was poured into ice water (500 ml), and extracted with ethyl acetate. The organic phase was combined, washed with saturated sodium bicarbonate solution three times, washed with saturated sodium chloride solution, and then dried by anhydrous sodium sulfate. The organic phase was then filtered to obtain a filtrate. The filtrate was concentrated to obtain a brown oily liquid 2-nitro-4,5-bis(2-methoxyethoxy)ethyl benzoate (14.10 g, 82.22%).

The synthetic route of 183322-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Salubris Pharmaceuticals Co., Ltd.; Shanghai Institute of Pharmaceutical Industry; LI, Jianqi; ZHANG, Zixue; XIE, Peng; ZHANG, Qingwei; EP2592083; (2013); 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. 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-methyl-2-phenylpropanoate

General procedure: The ester II was added to a mixture of NaOH (2.0 M, 8 mL) and methanol (10 mL)and stirred overnight at 65 C. After removal of methanol in vacuo, the residue wasdiluted with water and extracted with EtOAc (10 mL × 3). Then the pH value of thewater layer was adjusted to 2.0 with HCl (2.0 M) and extracted with EtOAc (30 mL ×3). The combined organic phases were evaporated in vacuo to give the crudecarboxylic acid III, which was used directly for the next step without furtherpurification.

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 57625-74-8.

Reference:
Article; Zhou, Danni; Wang, Chunxia; Li, Mingliang; Long, Zheng; Lan, Jingbo; Chinese Chemical Letters; vol. 29; 1; (2018); p. 191 – 193;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 22223-49-0, 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 22223-49-0 as follows.

A mixture of 2-amino-3-methylbenzoic acid (15.2 g, 0.10 mol), dimethylformamide (333 mL) and CsCO3 (49 g, 0.15 mol) was stirred at room temperature for about 40 minutes before drop wise addition of iodomethane (14.2 g, 6.2 mL, 0.10 mol) in dimethylformamide (“DMF”) (115 mL). The mixture was stirred . at room temperature overnight. The mixture was diluted with water (1 L), and extracted with diethyl ether. The aqueous phase was back extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous NaCI, dried over MgSO4, filtered and concentrated. The resultant material was dried at room temperature/0.5 mmHg to afford methyl 2-amino-3-methylbenzoate (17 g, 100%).To a solution methyl 2-amino-3-methylbenzoate (16.5 g, 0.10 mol) in CHCI3 (286 mL) was added acetic anhydride (23.5 g, 21.7 mL, 0.23 mol) so as to maintain the internal temperature <40 0C. The mixture was stirred at room temperature for 1 hour before addition of potassium acetate (2.94 g, 30 mmol) and isoamyl nitrite (25.8 g, 30 mL, 0.22 mol). The resultant mixture was heated at reflux overnight. To this was then added methanol (94 mL) and 6 N HCI (94 mL) and the mixture was stirred overnight. The reaction mixture was concentrated to provide an orange solid which was subsequently triturated with ethyl acetate and the solids were isolated by vacuum filtration. The solids were dried at room temperature/0.5 mmHg to afford methyl 1 H-indazole-7-carboxylate (15.4 g, 88%). -A solution of methyl 1 H-indazole-7-carboxylate (14.96 g, 84.9 mmol) in methanol (180 ml_) was cooled to 0 0C before addition of 29% aqueous potassium hydroxide (36 ml_). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The pH was adjusted to 5.5 using concentrated HCI. The volatiles were removed by vacuum filtration and the resultant material was suspended in water (100 mL) and ethyl acetate (200 mL). The resultant precipitate was isolated by vacuum filtration and rinsed with ethyl acetate. The solids were dried at room temperature/0.5 mmHg to afford the title compound (7.54 g, 55%).

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics