Tag: M.W=100-200

These common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, 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. Computed Properties of C10H12O2

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

The synthetic route of Methyl 2,6-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. Computed Properties of C9H8O4

Acetic acid benzo[1,3]dioxol-5-yl ester 15 (2.51g, 13.93mmol) was dissolved in glacial acetic acid (5mL), then a solution of concentrated HNO3 1.1mL (70%, d=1.413, 1.09g, 17.27mmol) in glacial acetic acid (2mL) was added dropwise. The reaction mixture was stirred at rt for 4h, then was cooled at 0C. The yellow solid was filtrated, washed with cold water, air-dried, and used in the next step without further purification (2.95g, yield 94%). 1H NMR (300MHz, CDCl3) delta: 2.37 (s, 3H), 6.15 (s, 2H), 6.65 (s, 1H), 7.60 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Brogi, Simone; Ramunno, Anna; Savi, Lida; Chemi, Giulia; Alfano, Gloria; Pecorelli, Alessandra; Pambianchi, Erika; Galatello, Paola; Compagnoni, Giulia; Focher, Federico; Biamonti, Giuseppe; Valacchi, Giuseppe; Butini, Stefania; Gemma, Sandra; Campiani, Giuseppe; Brindisi, Margherita; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 438 – 457;,
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Reference of 18355-74-3,Some common heterocyclic compound, 18355-74-3, name is Methyl 2,3-difluorobenzoate, molecular formula is C8H6F2O2, 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.

[000113] To a stirred solution of compound 44 (800 mg, 4.65 mmol) in DMF (10 mL) under inert atmosphere were added (4-methoxyphenyl) methanethiol 8 (282 mg, 5.11 mmol), cesium carbonate (1.66 g, 5.11 mmol) at RT and stirred for 6 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted water (25 mL) and extracted with ether (2 x 40 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 45 (750 mg, 53%) as an off- white solid. TLC: 20% EtOAc/ hexanes (R 0.4); 1H NMR (DMSO-d6, 500 MHz): oe 7.49-7.36 (m, 3H), 7.10 (d, J= 8.9 Hz, 2H), 6.79 (d, J= 8.9 Hz, 2H), 4.06 (s, 2H), 3.81 (s, 3H), 3.70 (s, 3H);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,3-difluorobenzoate, its application will become more common.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Synthetic Route of 39552-81-3, 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 39552-81-3 as follows.

EXAMPLE 3 N-(4-Methoxycarbonylmethylphenyl)-L-glutamine: Compound (3) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of methyl p-aminophenylacetate to give 13.38 g (88% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of methanol and 100 ml of water. To the solution was added 0.5 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.09 g (79% yield) of N-(4-methoxycarbonylmethylphenyl)-L-glutamine, m.p. 183.3-184.2 C. [alpha]D25 =+29.2 (c=1 2 N HCl)

According to the analysis of related databases, 39552-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); A;,
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Adding a certain compound to certain chemical reactions, such as: 66315-23-9, name is Ethyl 3-amino-4-(methylamino)benzoate, 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 66315-23-9, COA of Formula: C10H14N2O2

Step 1-1-4 Ethyl 1-methyl-1H-benzimidazole-5-carboxylate Ethyl 3-amino-4-methylaminobenzoate (24.1 g, 124 mmol) in the Step 1-1-3 was dissolved in formic acid (200 ml), and the solution was heated under reflux for 2 hours. After being cooled by ice, the solution was neutralized with a 25% ammonia water. The solution was subjected to extraction with chloroform, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (26.1 g, quantitative) as a light-purple powder. 1H-NMR (CDCl3) delta: 8.52 (d, J=1.5 Hz, 1H), 8.04 (dd, J=1.5, 8.5 Hz, 1H), 7.92 (s, 1H), 7.39 (d, J=8.5 Hz, 1H), 4.40 (q, J=7.3 Hz, 2H), 3.86 (s, 3H), 1.41 (t, J=7.3 Hz, 3H) Mass, m/z: 204 (M+), 159 (base)

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, Ethyl 3-amino-4-(methylamino)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
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Electric Literature of 53088-68-9, These common heterocyclic compound, 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, 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 96; Synthesis of (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester; Step 1: A mixture of (3-Chloro-phenyl)-acetic acid methyl ester (2.0 g, 10.8 mmol), N-bromosuccinimide (1.95 g, 11.0 mmol) and 3 drops of hydrobromic acid (48% solution) in chloroform (100 mL) was heated under reflux for three days. Additional amounts of N-bromosuccinimide and hydrobromic acid were added to drive the reaction to completion. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 10% ethyl acetate/hexanes gave Bromo-(3-chloro-phenyl)-acetic acid methyl ester (1.95 g, 69% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

The synthetic route of 53088-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); A1;,
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Reference of 1268830-91-6, 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. 1268830-91-6 name is Methyl 3-amino-6-fluoro-2-methoxybenzoate, 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 250 mL round bottom flask was charged with a solution of methyl 3-amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). A solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) was added to the reaction mixture over the course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, saturated aqueous sodium bicarbonate (100 mL) was added followed by stirring for 10 minutes. The aqueous mixture was extracted twice with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0- 30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)- benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, (CD3)2SO) delta = 9.27 (s, 1H), 7.48 (dd, J=9.1, 6.1, 1H), 7.09 (t, J=9.0, 1H), 3.89 (s, 3H), 3.85 – 3.74 (m, 3H), 3.29 (s, 15H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-fluoro-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
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Reference of 4720-83-6, These common heterocyclic compound, 4720-83-6, name is 6-Oxabicyclo[3.2.1]oct-3-en-7-one, 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 6-oxabicyclo [3.2. 1] oct-3-en-7-one (2.6 g, 21 mmol) in xylenes (50 ml) under nitrogen was added benzylamine (3.42 g, 32 mmol). The mixture was heated under reflux for 16 h, then cooled to room temperature. The heavy white precipitate was collected by filtration, and recrystallized from dichloromethane/hexane to give the amide as a white solid (3.8 g, 78%, m. p. 127- 128C)

The synthetic route of 4720-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGACEPT, INC.; WO2005/37832; (2005); A2;,
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13031-39-5, name is 3-Chlorophenyl acetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3-Chlorophenyl acetate

4-Chloro-2-hydroxyacetophenone.; 3-Chlorophenyl acetate (10 g, 0.0588 mol) was heated together with aluminum chloride (13.86 g, 0.105 mol) at 160 C for 2 hours. The mixture was poured on water and extracted with diethylether. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in methanol. The solution was treated with charcoal, filtered and water was added to the filtrate. The resulting oil was extracted with diethylether. The organic layer was dried over magnesium sulfate and diethylether was evaporated under reduced pressure. The resulting oil was used without further purification (77 %). IR (KBr) : u : 3436 (O-H), 3073 (C-H aromatic), 1643 (C=O) cni 1.

The synthetic route of 13031-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LIEGE; UNIVERSITE LIBRE DE BRUXELLES; WO2005/75463; (2005); A1;,
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Electric Literature of 210530-71-5, 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. 210530-71-5, name is Methyl 2-(3,4-difluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

2-(3,4-Difluorophenyl)acetylhydrazide (B4)(analogously to WO2004/101512A2, Bioorg. Med. Chem. Lett. 2004, 14(3), 817-822)1.0 g of methyl 2-(3,4-difluorophenyl)acetate (C4) is dissolved in 6.0 ml of 2-propanol. 365 mul of hydrazinium hydroxide are subsequently added, and the reaction solution is heated under reflux for 18 h overnight. The mixture is then evaporated to dryness in vacuo and purified by flash column chromatography on silica gel (solvent gradient: ethyl acetate/0-10% by vol. of ethanol), giving 803 mg of the title compound as a colourless solid having a melting point of 112 C.; MS: 187.1 (MH+); TLC: Rf=0.50 (ethyl acetate/ethanol 9:1 parts by volume).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(3,4-difluorophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/224302; (2011); A1;,
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