Tag: M.W=100-200

Synthetic Route of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

109 g (0.88 mol) of ethyl alpha, alpha-difluoroacetate was added to a stainless steel pressure-proof reaction vessel,0.107 g (0.18 mmol) of a ruthenium catalyst represented by the following formula42 g of sodium methoxide 28% methanol solution (0.22 mol of sodium methoxide)Methanol 290mL,The reactor was replaced with hydrogen 5 times,The hydrogen pressure was set to 1.0 MPa,After stirring at 15 C for 8 hours,React.After 19F-NMR analysis of the reaction, the conversion of alpha, alpha-difluoroacetic acid ethyl ester was 65%, and the selection of DFAL-EtOHThe rate is 91%. 19F-NMR was quantified with the internal standard substance alpha, alpha, alpha-trifluorotoluene.To the reaction solution was added 13.2 g (0.22 mol) of acetic acid,Then adjusting the pH to 8, judging that it is substantially neutral,Abort add.The liquid was directly distilled (bottom temperature ~ 66 C,Decompression degree ~ 2.1 kPa) to obtain a methanol solution containing DFAL-EtOH.The solution was distilled (theoretical plates 35 plates,Distillation temperature 92 ,Decompression degree ~ 35kPa) Most of the methanol separation.To a still pot (bottom) were added 96 g (2.08 mol) of ethanol,Continue distillation,45.9 g of DFAL-EtOH was obtained as a fraction.

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

Reference:
Patent; Center Xiaozi Co., Ltd.; Mu Cunzhenren; Qiu Yejinye; Wu Tianjiangzhang; Tian Zhongyishu; Teng Benyalong; (13 pag.)CN107438592; (2017); A;,
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Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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. Formula: C7H12O3

[0373] To a stirring ice-cooling solution of compound 72(200 mg, 1.39 mmol) and triethylamine (280 mg, 2.77 mmol)in DCM (10 ml), was added methanesulfonyl chloride (190mg, 1.66 mmol, dissolve in 1 ml DCM) dropwise. The reactionmixture was stirred 1 hat oo C., then diluted with DCM(20 ml), the organic phase was washed with water and brine,dried over Na2S04 , filtered and concentrated to afford crudecompound 73 (300 mg, yield 97%) as a colorless oil, useddirectly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.

Reference:
Patent; Gao, Daxin; Yang, Heping; Yu, Yajun; US2014/329800; (2014); A1;,
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Application of 349-43-9,Some common heterocyclic compound, 349-43-9, name is Ethyl 2-fluoropropionate, molecular formula is C5H9FO2, 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.

Syntheses of the intermediate sulfinamide esters A3.3 and A3.4A3.3 A3.4 In a dry apparatus under an inert atmosphere a solution of diisopropylamine (3.35 g, 101 mmol) in tetrahydrofuran (25 ml) was treated with n-butyl lithium (1.6M in hexane, 20.7 ml). The solution was stirred at -7 °C for 40 minutes. Thereafter, the solution was cooled to -75 °C and a solution of ethyl 2-fluoropropanoate (3.98 g, 33.2 mmol) in tetrahydrofuran (5 ml) was added dropwise. After 40 minutes a solution of chlorotitanium triisopropoxide (8.64 g, 33.2 mmol) in tetrahydrofuran (15 ml) was slowly added dropwise. After 40 minutes at -72 °C to the orange colored solution was added dropwise a solution of (R)-2-methyl-propane-2-sulfinic acid [l-(2-fluorophenyl)-(E)-ethylidene] -amide (intermediate A2.1) (4.0 g, 16.6 mmol) in tetrahydrofuran (5 ml). Stirring was continued at -72 °C for 4 hours, then the reaction mixture was kept at -20 °C for 17 hours. For the workup, the reaction mixture was quenched with an aqueous solution of ammonium chloride (13percent, 100 ml). The precipitate formed was diluted with water and the resulting mixture extracted three times with ethyl acetate. The organic layers were washed with brine, then combined, dried and evaporated at reduced pressure. Purification of the crude product by chromatography on silica gel using a 5:2-mixture auf heptane and ethyl acetate as the eluent yielded a l :2-mixture of the (2S,3R)-2-fluoro-3-(2-fluoro-phenyl)-2-methyl-3- ((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.3) and (2R,3R)-2-Fluoro-3- (2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.4) (4.43 g, 74percent) as a light yellow oil. MS (ISP): m/z = 362.2 [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 Ethyl 2-fluoropropionate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; HILPERT, Hans; WOSTL, Wolfgang; WO2012/139993; (2012); A1;,
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Application of 10601-80-6, 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 10601-80-6 as follows.

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL×3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

According to the analysis of related databases, 10601-80-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Synthetic Route of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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: Preparation of Copper Acetylides; Procedure 1To a solution of CuI (3.8 g, 20.0 mmol) in a mixture of NH4OH(28% NH3 solution, 50 mL) and EtOH (30 mL) was added the alkyne1 (10.0 mmol) dropwise. The deep blue reaction mixture wasstirred overnight at r.t. under argon and the yellow precipitate wascollected by filtration and successively washed with NH4OH (10%NH3 solution, 3 × 50 mL), H2O (3 × 50 mL), EtOH (3 × 50 mL), andEt2O (3 × 50 mL). The bright yellow solid was then dried under highvacuum overnight to afford the desired polymeric copper acetylide2, which was used without further purification.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
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Synthetic Route of 217314-47-1, 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. 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(i) Methyl 3-((4-((4-((tert-butoxycarbonvnamino)naphthalen-1-yl)oxy)pyridin-2-yl)amino)-5-methoxybenzoateA flask charged with tert-butyl (4-((2-chloropyridin-4-yl)oxy)naphthalen-1-yl)carbamate (see Example 2(ii) above; 20.1 g, 54.2 mmol), methyl 3-amino-5-methoxybenzoate (10.80 g, 59.6 mmol), BrettPhos G1 Precatalyst (550 mg, 0.689 mmol) and K2C03(14.98 g, 108 mmol) in anhydrous tBuOH (300 ml.) was back filled with nitrogen (x3) and then placed on a heating block (preheated to 90C). The suspension was degassed with nitrogen, stirred for 8 h and then cooled to rt and stirred for 8 h. Reaction mixture was warmed to 50C then cooled to rt and diluted with DCM (1 L), the suspension was filtered through Celite and the solvent evaporated. The brown oil was sonicated with diethyl ether (500 ml.) and the solid filtered under suction, washing with further diethylether, to afford the sub-title compound (21.55 g) as a beige solid. 1H NMR (400 MHz, DMSO-d6) delta 9.37 (s, 1 H), 9.19 (s, 1 H), 8.15 (s, 1 H), 8.13 (s, 1 H), 7.85 (dd, 1 H), 7.76 (dd, 1 H), 7.69 (dd, 1 H), 7.66-7.54 (m, 3H), 7.37 (d, 1 H), 6.96 (dd, 1 H), 6.62 (dd, 1 H), 6.09 (d, 1 H), 3.82 (s, 3H), 3.75 (s, 3H), 1.53 (s, 9H). (90% purity). LCMS m/z 516 (M+H)+(ES+); 514 (M-H)”(ES”)

The synthetic route of Methyl 3-amino-5-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; BAKER, Thomas Matthew; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; RIGBY, Aaron; WO2015/92423; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, 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 18595-18-1, Quality Control of Methyl 3-amino-4-methylbenzoate

To a suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (4.09 g, 25.3 mmol) in dichloromethane (100 mL) and DMF (0.25 mL) at 0 C was added oxalyl chloride (4.15 mL, 48.0 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS. The reaction was subsequently reduced to dryness and suspended in dichloromethane (100 mL) and was added a solution of methyl 3-amino-4-methylbenzoate (2) (4.6 g, 27.9 mmol) in dichloromethane (100 mL) and triethylamine (7.1 mL) . Contents were stirred at room temperature for 4 hours and diluted with dichloromethane (100 mL). The reaction was washed with water, saturated NaHC03, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and dried to afford methyl 3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4- methylbenzoate (3) as a white solid. MS m/z 310.1 (M+1 ) +.

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

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2967-93-3, name is Methyl 2-fluoro-5-methylbenzoate, 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 2967-93-3, Computed Properties of C9H9FO2

The 2-fluoro-5-methyl benzoic acid methyl ester (100 mg, 0 . 60mmol), NBS (112 mg, 0 . 63mmol), AIBN (60 mg, 0 . 36mmol) is added in the reaction bottle, by adding CCl4(5 ml), Ar atmosphere reflow 3h, raw material a small amount of residual, reducing pressure and evaporating solvent, adding anhydrous ethyl ether (10 ml), vacuum filtration, filtrate turns on lathe does, column chromatography, to obtain 20 mg of white solid, yield 13.5%.

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 2-fluoro-5-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute Of Materia Medica Chinese Academy Of Medical Sciences; Xu, Bailing; Chen, Xiaoguang; Yao, Haiping; Ji, Ming; Jin, Jing; Zhou, Jie; Wang, Ke; Zhao, Dalong; (55 pag.)CN105461697; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 606-45-1, name is Methyl 2-methoxybenzoate, 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 606-45-1, category: esters-buliding-blocks

General procedure: Various benzohydrazides 5-7 and 9-13 were obtained accordingto known procedures [40,65] except for benzohydrazides 4and 8 which were commercially available. A solution of the methylbenzoate (1 equiv) in ethanol was added dropwise to 65% hydrazinemonohydrate (5 equiv). The reaction mixture was then heatedunder reflux and stirred overnight. The reaction progress was followedup by TLC. Crude product was collected by filtration aftercooling of the reaction medium and finally washed with coldethanol unless specified otherwise. The desired benzohydrazides were used without any further purification.The analysis of spectral data (1H and 13C NMR), the yields, HRMS,Mp and Rf of these precursors are presented in SupplementaryInformation.

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

Reference:
Article; Ameryckx, Alice; Thabault, Leopold; Pochet, Lionel; Leimanis, Serge; Poupaert, Jacques H.; Wouters, Johan; Joris, Bernard; Van Bambeke, Francoise; Frederick, Raphael; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 324 – 338;,
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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. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-amino-4-methoxylbenzoate

To a solution of compound 1 (50 g, 276 mmol) in CHCb (600 mL) was added SO2CI2 (26 mL, 331 mmol) in an ice bath and stirred at reflux for 4 hours. The reaction mixture was concentrated to afford the crude product, which was purified by trituration with PE/EA = 1 : 1 (200 mL) to get desired product as white solid (36 g, 61% yield). 1H MR (400 MHz, DMSO-d6) delta: 7.64 (IH, s), 6.48 (IH, s), 3.81 (3H, s), 3.75 (3H, 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 50413-30-4.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); A1;,
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