Category: esters-buliding-blocks

Electric Literature of 609-12-1, These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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.

Under an atmosphere of nitrogen, an ice-cooled solution of 6-methoxyisoindolin-1-one (commercially available from for example Astatech) (105 mg, 0.64 mmol) in DMF (2.5 mL) was treated with sodium hydride (60% w/w in mineral oil) (31 mg, 0.77 mmol) and the mixture was allowed to warm to ambient temperature. The mixture was then treated with ethyl 2-bromo-3-methylbutanoate (commercially available from for example Alfa Aesar) (135 mg, 0.64 mmol) and the mixture was stirred for 18 hours then cautiously treated with saturated aqueous ammonium chloride (20 mL). The product was extracted with ethyl acetate (2*25 mL) and the combined organic phase was washed with water (20 mL), brine (20 mL), filtered through a hydrophobic fit and evaporated to dryness. the product was purified by flash chromatography (20 g silica cartridge) using a gradient elution from 0 to 50% ethyl acetate in cyclohexane to afford the title compound (40 mg, 21% yield). LCMS RT=1.03 min, ES+ve m/z 292 [M+H]+

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Crews, Craig M.; Buckley, Dennis; Ciulli, Alessio; Jorgensen, William; Gareiss, Peter C.; Van Molle, Inge; Gustafson, Jeffrey; Tae, Hyun-Seop; Michel, Julien; Hoyer, Dentin Wade; Roth, Anke G.; Harling, John David; Smith, Ian Edward David; Miah, Afjal Hussain; Campos, Sebastien Andre; Le, Joelle; US2014/356322; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3196-15-4, name is Methyl 2-bromobutyrate, 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 3196-15-4, Safety of Methyl 2-bromobutyrate

To a solution of naphthalene-2,7-diol (5.0 g, 31 mmol) in acetone (200 mL) was added cesium carbonate (10.1 g, 31 mmol) at room temperature under a nitrogen atmosphere with stirring. After the addition, the mixture was stirred at room temperature for 3 min and then methyl-2-bromobutyrate (5.6 g, 31 mmol) was added. The mixture was stirred at room temperature overnight and then filtered to remove solids. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 80 % as eluents) to give the title compound (3.9 g) as a solid. in NMR (CDCI3) delta 7.62-7.70 (m, 2H), 6.85-7.05 (m, 4H), 5.85 (s, 1H), 4.68-4.78 (m, 1H),3.75 (s, 3H), 2.00-2.10 (m, 2H), 1.08-1.15 (t, 3H).

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CREWS, Alvin, Donald, Jr.; DING, Amy, X.; TSENG, Chi-Ping; WO2012/87372; (2012); A1;,
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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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H11BrO2

General procedure: A mixture of 17 (257 mg, 1.1 mmol), ethyl1-bromocyclobutanecarboxylate (266 mg, 1.3 mmol) and Cs2CO3(371 mg, 1.1 mmol) in DMF was heated to 60 C and stirred for 2 hours. The mixture was cooled to room temperature and the resulting precipitate was filtered off. The collected filtrate was concentrated to give the ester ethyl1-((6-bromoquinolin-4-yl) thio)cyclobutanecarboxylate as an oil (300 mg, 77%).

According to the analysis of related databases, 35120-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Peng, Jianbiao; Hu, Qiyue; Gu, Chunyan; Liu, Bonian; Jin, Fangfang; Yuan, Jijun; Feng, Jun; Zhang, Lei; Lan, Jiong; Dong, Qing; Cao, Guoqing; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 277 – 282;,
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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. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, A new synthetic method of this compound is introduced below., Formula: C10H6F3NO2

General procedure: To synthesize Boc-Gly-AFC, 1 eq of Boc-Gly-OH and 1 eq of AFC2 were dissolved in anhydrous pyridine and cooled in a ice/NaCl bath to 15 C. To this mixture 1.4 eq of POCl3 was added dropwise in 10 min. The reaction was carried out at -15 C and the progress was monitored using TLC analysis. After the reaction was complete (60 min) the mixture was dissolved in ethyl acetate and extracted with 5% citric acid (2x), 5% NaHCO3 (2x),and brine (2x). The organic fraction was dried over MgSO4 and ethyl acetate was then removed under reduced pressure to obtain Boc-Gly-AFC, which was used for further synthesis without additional purification. In a separate synthesis N-acetylated tripeptides with the free carboxylic group at the C terminus were synthesized similarly as described previously and used without further purification (41). To synthesize Ac-peptide-Gly-AFC substrates, 1 eq of Boc-Gly-AFC was dissolved in 50% TFA in dichloromethane (with 2.5% of triisopropylsilane as a scavenger) and the Boc deprotection reaction was carried out for 30 min. After the reaction was completed, TFA and dichloromethane were removed under reduced pressure to obtain NH2-Gly-AFC. Next, NH2-Gly-AFC was dissolved solved in a minimal amount of N,N-dimethylformamide, followed by the addition of 1 eq of Ac-peptide-COOH and 1 eqof HBTU (O-benzotriazole-N,N,N’,N’-tetramethyluronium hexafluorophosphate). Finally, 3 eq of DIPEA (N,N-diisopropylethylamine) were added and the coupling reaction was carried out for 3 h. After the reaction was completed, as judged by HPLC analysis, the mixture was diluted in ethyl acetate and extracted with 5% citric acid (2x), 5% NaHCO3 (2x), and brine (2x). The organic fraction was dried over MgSO4 and the ethyl acetate was then removed under reduced pressure to obtain crude Ac-peptide-Gly-AFC. Next, all protecting groups were removed in 50% TFA in dichloromethane (with 2.5% of triisopropylsilane as a scavenger) for 1 h. Finally, the crude productwas purified by HPLC on a Waters M600 solvent delivery module with a Waters M2489 detector system using a semi-preparative Waters Spherisorb S10ODS2 column. The solvent composition was as follows: phase A (water, 0.1% TFA) and phase B (acetonitrile, 0.1% TFA). The purity of each compound was verified by an analytical HPLC system using a Waters Spherisorb S5ODS2 column. The molecular weight of each Ac-peptide-Gly-AFC substrate was determined by high-resolutionmass spectrometry using a High Resolution Mass Spectrometer WATERS LCT premier XE with Electrospray Ionization (ESI) and Time of Flight (TOF) module.

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:
Article; Rajkovi?, Jelena; Poreba, Marcin; Cagli?, Dejan; Vidmar, Robert; Wilk, Aleksandra; Borowik, Agata; Salvesen, Guy; Turk, Vito; Drag, Marcin; Turk, Boris; Journal of Biological Chemistry; vol. 290; 47; (2015); p. 28231 – 28244;,
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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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 37746-78-4

General procedure: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 × 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 × 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].

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 37746-78-4.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
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957207-58-8, name is Methyl 4-bromo-2-(trifluoromethyl)benzoate, 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. SDS of cas: 957207-58-8

Example 6: Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) (0215) (0216) To a 100 mL round-bottomed flask was added 90 methyl 4-bromo-2-(trifluoromethyl)benzoate (2.25 g, 8.00 mmol), 91 (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 92 1,3-dimethylimidazolidin-2-one (40 mL). 65 Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), 59 copper(I) iodide (0.0760 mg, 0.400 mmol), and 93 cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. 70 Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash column chromatography provided the 94 title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta ?59.92, ?108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).

The synthetic route of 957207-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Barton, Thomas; Gao, Xin; Hunter, Jim; LePlae, Paul R.; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (176 pag.)US2017/208806; (2017); A1;,
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Application of 2967-66-0, The chemical industry reduces the impact on the environment during synthesis 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

General procedure: In an argon filled glove-box, a ca. 80 ml. Premex stainless steel autocalve fitted with a PTFE in- ner chamber and a PTFE coated magnetic stirring bar was charged with Ru(L)CO (I) (6×10-3 mmol, 4.7 mg), the specified ester (0.6 mmol), degassed, anhydrous 1 ,4-dioxane (6.0 ml.) and degassed anhydrous methanol (0.05 ml_). Hexamethylbenzene (0.15 mmol, as internal stand- ard) was added and the mixture was stirred vigorously at room temperature until full dissolution. A sample (0.1 ml.) was then taken for to-analysis (GC and NMR). After closing the reaction ves- sel was removed from the glove-box. The argon atmosphere in the autoclave was replaced with H2 by twice pressurization to 30 bar, and pressure release at room temperature. The autoclave was then pressurized with H2 gas (60 bar). The solution was heated at 130 C (heating mantel temperature) with stirring for 17 hrs. After cooling to 0 C, the system was vented carefully and purged for 1 minute with argon. A sample of the crude mixture (0.1 ml.) was transferred to a vial and was analyzed as-is by GC on an Agilent Technologies 6890N gas chromatography system equipped with a FID detector and an Agilent Technologies DB-1 capillary column (30 m x 0.250 mm / 1.0 pm). Another sample (0.1 ml.) was diluted with CDCI3 (0.6 ml.) in an NMR tube and analyzed by 1H-NMR. Conversion was determined by comparison to the samples at to (with hex- amethylbenzene as internal standard). NMR yield was determined by the ratio of product to starting material in the crude sample after reaction.

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-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; SCHAUB, Thomas; ANABY, Aviel; SCHELWIES, Mathias; PACIELLO, Rocco; SCHWABEN, Jonas; HASHMI, A. Stephen K.; (44 pag.)WO2019/138000; (2019); A1;,
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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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 87-13-8

2-Phenylaminomethylene-malonic acid diethyl ester A mixture of aniline (25.6 g, 0.28 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.29 mol) was heated at 140-150 C. for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. 1H NMR (d-DMSO) delta 11.00 (d, 1H), 8.54 (d, J=13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

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 87-13-8.

Reference:
Patent; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); A1;,
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Reference of 1150566-27-0, 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 1150566-27-0 as follows.

(2R,4S)-4-Fluoro-2-[3-fluoro-5-(methylsulfanyl)phenyl]pyrrolidine hydrochloride (Preparation 25, 23.75 g, 89.4 mmol), KF (46.73 g, 804.3 mmol), ethyl 6- chloroimidazo[1 ,2-b]pyridazine-3-carboxylate (19.76 g, 87.6 mmol) were suspended in DMSO (350 ml). The reaction was heated at 130C for 82 h. The reaction mixture was allowed to cool to rt before being poured into distilled water (750 ml), which precipitated a beige solid. The liquid was decanted and the solid was washed with distilled water three times (3 x 250 ml). The beige solid was taken up in MTBE (500 ml) and partitioned between sat. aq. NH4CI (500 ml) and then finally brine (500 ml). The organic layer was dried (Na2S04), filtered and concentrated in vacuo to afford a dark reddish residue which was used without further purification (30.52 g, 82 %). LCMS m/z = 419 [M+H]+

According to the analysis of related databases, 1150566-27-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BENEVOLENTAI BIO LIMITED; BROWN, Alan; GLEN, Angela; (115 pag.)WO2020/39209; (2020); A1;,
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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. 34812-95-8, name is Di-tert-butyl 2-methylmalonate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H22O4

[00129] To a salted ice (-10 – 0C) cooled solution of UB-12527 (20.0g, 86.8mmol, 1.0 equiv., in 190ml of dry tetrahydrofuran) 3.47g (86.8mmol, l.Oequiv., 60% in mineral oil) of sodium hydride was added. The mixture was warmed to room temperature then stirred for 30min. To the resulting white suspension 15.5ml (130mmol, 1.5equiv.) of 1,4- dibromobutane was added and the mixture was stirred overnight. The mixture was evaporated and the residue was dissolved in 250ml of water and 250ml of MTBE. The phases were separated, the organic was dried over sodium sulfate and evaporated. The crude product was purified by rectification (0.7-0.8mbar, 111-125C). Yield: 14.4g (39.5mmol, 45.5%) colourless, clear oil. GC: 96.7%.

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; APOSENSE LTD.; VAN GELDER, Joel M.; LEVY, Menashe; ARGOV, Mirit; BEN-AMI, Miri; ZIV, Ilan; WO2013/150534; (2013); A1;,
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