Esters-buliding-blocks

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. 1195768-18-3 name is Methyl 3-amino-2-fluorobenzoate, 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. 1195768-18-3

A 500 mL round-bottomed flask was charged with methyl 3-amino-2- fluorobenzoate (20 g, 1 18 mmol) and pyridine (10.52 mL, 130 mmol) in dichloromethane (DCM) (100 mL) to give a yellow/clear solution at 0 C. After 5 min, 1 -propanesulfonyl chloride (13.26 mL, 1 18 mmol) was added to the reaction and warmed to room temperature. After 24 h, the reaction mixture was diluted with EtOAc (200 mL) and concentrated to a volume of 50 mL. The reaction mixture was diluted with EtOAc (200 mL) and water (200 mL) and stirred. After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was diluted with water (200 mL). After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was dried over Na2SO4, filtered, and concentrated to 50 mL. While stirring, the reaction mixture was diluted with EtOAc (50 mL) and hexanes (200 mL) and stirred. The solids were filtered and washed with hexanes. The product was put into drying oven for 1 day to obtain methyl 2-fluoro-3- [(propylsulfonyl)amino]benzoate. 28.9 g (105 mmol, 89 % yield) MS: 276 [M+H]+.

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

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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13831-03-3, Name is tert-Butyl propiolate, 13831-03-3, 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.

Step 3: 1 -[4-(tert-Butyl-dimethyl-silanyloxymethyl)-benzyl]-1 H-[1 ,2,3]triazole-4- carboxylic acid tert-butyl ester. Cupric sulfate pentahydrate (1 .03 g, 4.1 1 mmol) and sodium ascorbate (4.07 g, 20.6 mmol) are added to a stirred solution of (4-azidomethyl-benzyloxy)-tert-butyl-dimethy- silane (6.0 g, 20.6 mmol) and tert-butyl propiolate (3.10 ml, 22.6 mmol) dissolved in a mixture of 50 ml of tert-butanol and 50ml of water. The reaction mixture is stirred at room temperature for 2 hours. The solvent is removed under reduced pressure and the residue is partitioned between water and DCM. The organic layer is separated and concentrated under reduced pressure to obtain the crude title compound (Yield 8.3 g). LC (Method 4): tR = 0.73 min; Mass spectrum (ES+): m/z = 404 [M+H]+.

Statistics shows that tert-Butyl propiolate is playing an increasingly important role. we look forward to future research findings about 13831-03-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, 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 6065-82-3. 6065-82-3

I) diethoxyacetic acid To a solution of ethyl diethoxyacetate (5.00 g) in ethanol (20 mL) was added 1M aqueous sodium hydroxide solution (60 mL). The reaction mixture was stirred at room temperature for 2 hr, and ethanol was evaporated under reduced pressure. An aqueous solution of the residue was washed with diethyl ether, and adjusted to pH 3-4 with 2M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.00 g). 1H NMR (400 MHz, CDCl3) delta 1.27 (6H, t, J=7.2 Hz), 3.64-3.77 (4H, m), 4.96 (1H, s), 8.91 (1H, br s).

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 Ethyl diethoxyacetate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1559-02-0, Adding some certain compound to certain chemical reactions, such as: 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, 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 1559-02-0.

Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate-A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (12 mL, 12 mmol, 2.2 equiv) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (1.0 mL, 5.7 mmol, 1.0 equiv) in tetrahydrofuran (19 mL) at 23 C. The resulting solution was heated to 65 C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (100 mL) and extracted with ethyl acetate (4*50 mL).

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 1559-02-0.

Reference:
Patent; Parker, Marshall H.; Yap, Maurice C.H.; Eckelbarger, Joseph D.; Buysse, Ann M.; Babcock, Jonathan M.; Hunter, Ricky; Adelfinskaya, Yelena; Samaritoni, Jack G.; Garizi, Negar; Trullinger, Tony K.; US2012/53146; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 25597-16-4

[0179] A mixture of benzaldehyde from Step 1 (3.0 g, 18.07 mmole) and ethyl 4,4, 4- trifluorocrotonate (4.5 g, 27.11 mmole) was dissolved in anhydrous DMF (20 mL), warmed to 60 C and treated with anhydrous K2CO3 (4.99 g, 36.14 mmole). The solution was maintained at 90 C for 24 hours. LCMS analysis indicated that the reaction was complete. After the reaction was cooled to room temperature, the solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MGS04, filtered and concentrated IRA VACUA to afford brown solid, that was dissolved in MeOH (40 mL) and was precipitated upon adding 13 mL water. The suspension was filtered and dried 1 on vacuum yielding a light brown solid: (4.37 g, 76.6 %): LCMSNL/Z339. 10 (M+Na). H NMR (CDC13/400 MHz) 7.68 (s, 1H), 7.03 (d, 1H, J=8. 7 Hz), 6.50 (d, 1H, J=8. 7 Hz), 5.70 (q, 1H, J=6 Hz), 4.29 (q, 2H, J= 7.2 Hz), 3.84 (s, 3H), 2.09 (s, 3H), 1.33 (t, 3H, J=7. 2 Hz).

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, 25597-16-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

541-16-2, 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 541-16-2 as follows.

2) Preparation of 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one After 55% sodium hydride (322 mg, 7.38 mmol) was added to a solution of di-tert-butyl malonate (970 mg, 4.48 mmol) in N,N-dimethylformamide (10 mL), 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphen yl)-2H-pyridazin-3-one (1.8 g, 4.90 mmol) was added under ice-cold stirring. The reaction mixture was stirred at room temperature for 1 hour, poured into water, and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was isolated and purified by chromatography on silica gel (hexane/ethyl acetate=3/1) to yield the title compound as a yellow powder (yield: 1.39 mg, 61.8%). 1H NMR (400 MHz, CDCl3) delta: 0.44-0.50 (2H, m), 0.50-0.58 (2H, m), 1.41 (18H, s), 1.56 (1H, m), 3.12 (2H, d, J=7.8 Hz), 3.87 (1H, t, J=7.8 Hz), 3.94 (3H, s), 4.09 (2H, d, J=7.8 Hz), 7.01 (1H, dd, J=8.5, 8.5 Hz), 7.43 (1H, d, J=8.5 Hz), 7.50 (1H, s), 7.57 (1H, dd, J=12.4, 2.2 Hz).

According to the analysis of related databases, Di-tert-Butyl malonate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOWA CO., LTD.; US2004/2497; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 5026-62-0, name is Sodium 4-(methoxycarbonyl)phenolate, 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 5026-62-0. 5026-62-0

EXAMPLE 60 1,4-Bis(1,3-benzodioxol-5-yloxy)-2-methyl-2-butene 3.2 g (0.02 mol) of sodium salt of 3,4-methylendioxyphenol are suspended in 60 cc of 1,2-dimethoxyethane and cooled to 0-5. 2.28 g (0.01 mol) of 1,4-dibromo-2-methyl-2-butene, dissolved in 20 cc of 1,2-dimethoxyethane are added while stirring. The mixture is stirred at 20-25 during the course of 20 hours and at 50 during the course of 5 hours; it is subsequently filtered and the filtrate is evaporated. The residue is taken up in ether, extracted with saturated salt solution, the ether phase is dried with sodium sulphate and evaporated. The obtained viscous oil is purified by chromatography on silica gel with hexane/ethyl acetate 5: 1 and subsequently by crystallization from ethyl acetate/hexane. M.P. 73.5-74. In analogous manner as described in Example 60, but using sodium salt of 4-hydroxy-benzoic methyl ester in the place of the sodium salt of 3,4-methylendioxy-phenol, the following compound is produced.

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 Sodium 4-(methoxycarbonyl)phenolate.

Reference:
Patent; Sandoz Ltd.; US3978134; (1976); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

37466-90-3, These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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.

Synthesis of 2-Oxo-2,3-dihydro-lH-benzoimidazole-5-carboxylic acid ethyl ester ’22a): 3,4-Diamino-benzoic acid ethyl ester (100 mg, 0.56 mmol) was dissolved in 5 mL of IHF and cooled to 00C. Triethyamine (77 muL, 0.56 mmol) was added followed by potassium carbonate (230 mg, 1.68 mmol). Triphosgene (82 mg, 0.28 mmol) was added in one portion, md the reaction mixture was then warmed up to room temperature and quenched with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine and dried over MgSO4. Solvent was then removed and the residue was purified by column chromatography (60% ethyl acetate/hexanes). The product (92 mg, 80%) was obtained as a white solid. MS (ES) M+H expected = 207.1, found = 207.1.

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 37466-90-3.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2007/51062; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

455-75-4, A common compound: 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of ethyl 3-amiotano-4-fluorobenzoate (547 g, 30 mmol) and pyridine (2 55 mL, 33 mmol) in DCM (150 mL) was added 2,6-diotafluorobenzenesulfonyl chloride (4 45 mL, 33 mmol) The reaction was stirred overnight at rt After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7 87 g (66% yield) of the product of Step A as a white powder ES-LCMS m/z 360 (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, Ethyl 3-amino-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, 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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-amino-3-methyl-benzoate (12.17 g, 73.70 mmol) in DCM (135 mL) was added 1-pyridin-1-ium-1-yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (30.14 g, 81.00 mmol). The reaction mixture was stirred for 1.5h, then 1-pyridin-1-ium-1- yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (2.740 g, 7.367 mmol) was added and the mixture was stirred for another 2h, then quenched with aqueous saturated NaHCO3 (100 mL).The layers were separated. The aqueous layer was extracted with DCM (2 x 100 mL). The combined organic extracts were washed with aqueous 1M Na2S2O3 (100 mL) and dried over Na2SO4, filtered and concentrated. The crude residue was co-evaporated with heptane (2x) and purified by flash chromatography on a BiotageTM snap 340g silica cartridge, using a gradient of EtOAc (0-25%) in Hex as eluent. The fractions were combined and concentrated to provide thetitle compound (18.0 g, 84% yield). ?H NMR (400 MHz, CDC13) oe 8.23 (s, 1H), 7.71 (s, 1H),4.51 (s, 2H), 3.85 (s, 3H), 2.25 (s, 3H).

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; VERTEX PHARMACEUTICALS INCORPORATED; GALLANT, Michel; TRUCHON, Jean-Francois; REDDY, Thumkunta, Jagadeeswar; DIETRICH, Evelyne; VAILLANCOURT, Louis; VALLEE, Frederic; (131 pag.)WO2016/199105; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics