Month: June 2021

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 75567-84-9 as follows. Safety of Methyl 3-(4-bromophenyl)propanoate

General procedure: Methyl 3-(4-bromophenyl)propanoate31 1 (1.0 equiv) and the appropriate commercially available (substituted-phenyl)boronic acid (1.5 equiv) were dissolved in a mixture of dioxane/EtOH (1:1) (concentration 1 mL/mmol) and 1 M aqueous NaHCO3 (2.0 equiv). To the solution, Pd(PPh3)4 (2.5 mol %) was added and the mixture was heated in the microwave at 100 C for 3 h, after which TLC showed full conversion. The reaction mixture was concentrated in vacuo, acidified to pH = 1 using 1 M HCl (aq), extracted with EtOAc, dried over MgSO4 and concentrated under reduced pressure. Purification by column chromatography eluting with CH2Cl2/Pet. ether (2:1) yielded the desired biphenyl esters as solids.

According to the analysis of related databases, 75567-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Van Veldhoven, Jacobus P.D.; Liu, Rongfang; Thee, Stephanie A.; Wouters, Yessica; Verhoork, Sanne J.M.; Mooiman, Christiaan; Louvel, Julien; Ijzerman, Adriaan P.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 4013 – 4025;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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. Recommanded Product: trans-Ethyl 4-hydroxycyclohexanecarboxylate

VII) Synthesis of CP30450-3; Ethyl 4-[(/erf-butyldimethylsilyl)oxy]cyclohexanecarboxylate (55); Following protocols reported by Wild,10 a solution of Ethyl 4- hydroxycylohexanecarboxylate (54) (1.0 mL, 6.20 mmol) in DMF (3.0 mL) was treated with imidazole (929 mg, 13.6 mmol) and tert-butyldimethylsilyl chloride (1.22 g, 8.09 mmol) and the resulting mixture stirred magnetically at 18 °C under a nitrogen atmosphere for 20 h. The reaction mixture was then treated with Et2O (50 mL), washed with HCl (1 x 5 mL of a 1 M aqueous solution), then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (hexane- 1:49 v/v ethyl acetate/hexane gradient elution) to afford a ca. 1:1 mixture of the cis- and troens-isomeric forms of the title compound 55 (1.78 g, quant.) as a colourless oil, Rf 0.7 in 3:7 v/v ethyl acetate/hexane.1H NMR (300 MHz) delta 4.12 and 4.11 (2 x q, J 7.1 and 7.1 Hz, 2 x 2H), 3.89 and 3.56 (2 x m, 2 x IH), 2.33-2.16 (complex m, 2 x IH), 1.98-1.87 (complex m, 2 x 2H), 1.68-1.22 (complex m, 2 x 6H), 1.25 and 1.24 (2 x t, J 7.1 and 7.1 Hz, 2 x 3H), 0.88 and 0.87(8) (2 x s, 2 x 9H), 0.05 and 0.03 (2 x s, 2 x 6H).13C NMR (75 MHz) delta 175.8 and 175.7 (2 x C), 70.5 and 66.6 (2 x CH), 60.1 and 60.0 (2 x CH2), 42.2 and 42.0 (2 x CH), 34.8 and 32.8 (4 x CH2), 27.2 and 23.4 (4 x CH2), 25.8 and 25.7(7) (6 x CH3), 18.2 and 18.1 (2 x C), 14.2 (2 x CH3), -4.7 and -4.9 (4 x CH3). IR vmax/cm”1 2934, 2858, 1734, 1463, 1252, 1096, 1049, 835, 774.Mass Spectrum (EI) m/z 229 [(M-C4Hg)+’, 92], 57 (100).HRMS found: (M-C4H9)+\ 229.1256. C15H30O3Si requires (M-C4Hg)+’, 229.1260.

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

Reference:
Patent; CRYPTOPHARMA PTY LTD; WO2008/124878; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3697-68-5, The chemical industry reduces the impact on the environment during synthesis 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of ethyl l-(hydroxymethyl)cyclopropane-l-carboxylate (3.0 g, 21 mmol) in DCM (50 mL) at -10 C was added DAST (6.0 g, 40 mmol) under Ar. The reaction mixture was stirred as it warmed to ambient temperature over 1 h and continued to stir at that temperature for 23 h. An aqueous solution of HC1 (10%, 5 drops) and H20 (50 mL) were added, and the layers were separated. The aqueous layer was extracted with DCM (50 mL) and the combined organic phases were washed sequentially with H20 (50 mL) and brine (50 mL), dried (MgS04), and filtered. The filtrate was concentrated in vacuo to give ethyl l-(fluoromethyl)cyclopropane-l- carboxylate (3.0 g, yield:99%), which was carried forward without further purification.

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 1-(hydroxymethyl)cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, 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. Safety of Benzyl 4-bromobutanoate

REFERENCE EXAMPLE 33 A mixture of 4-bromobutyric acid benzyl ester (23.7 g), imidazole (8.1 g), potassium carbonate (14.0 g) and acetone (400 ml) was stirred under refluxing conditions for 6 hours. After the reaction mixture was cooled to room temperature, the insoluble solid was filtered off, the filtrate was concentrated. The residual oily substance was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (20:1, v/v) to yield 4-(1-imidazolyl)butyric acid benzyl ester (7.3 g, 33%) as an oily substance. NMR (delta ppm in CDCl3): 2.11 (2H, m), 2.34 (2H, t, J=6.8 Hz), 3.99 (2H, t, J=6.8 Hz), 5.12 (2H, s), 6.87 (1H, S), 7.05 (1H, s), 7.30-7.40 (5H, m).

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

Reference:
Patent; Takeda Chemical Industries; US5436247; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 193A(+/-)-tert-Butyl 1-[(3-bromo-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 42.2 ml (105.5 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 14.8 ml (105.5 mmol) of diisopropylamine in 60 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 12.0 g (84.4 mmol) of tert-butyl cyclopropanecarboxylate in 60 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 15.4 g (70.3 mmol) of 3-bromo-4-chlorobenzaldehyde in 60 ml of abs. THF was added. The reaction mixture was slowly warmed to RT overnight, saturated aqueous ammonium chloride solution was then added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1?10:1). This gave 16.2 g of the target compound (52.5% of theory).LC-MS (Method 4): Rt=1.47 min; m/z=286/288.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.84-0.99 (m, 2H), 1.02-1.17 (m, 2H), 1.24 (s, 9H), 4.88 (d, 1H), 5.55 (d, 1H), 7.39 (dd, 1H), 7.57 (d, 1H), 7.71 (d, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 131001-86-0, name is Methyl 2-bromo-3-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 131001-86-0, SDS of cas: 131001-86-0

25 mi (10.0 MMOL) of aqueous 0.4 M sodium carbonate solution and then 303 mg (0.26 MMOL) OF TETRAKIS (TRIPHENYLPHOSPHINE) PALLADIUM (0) are added to a solution of 2.0 g (8.7 MMOL) of methyl 2-BROMO-3-METHYLBENZOATE and 2.16 g (10.5 MMOL) of 4- (trifluoromethoxy) boronic acid in 25 ml of acetonitrile. The mixture is refluxed overnight; after cooling, the reaction medium is diluted with 50 ml of water and extracted with diethyl ether. The combined organic extracts are washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by flash chromatography (eluent : 5% of diethyl ether in hexane) to give 2.4 g (89%) of the title compound.

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; MERCK PATENT GMBH; WO2004/37806; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 431-47-0,Some common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, molecular formula is C3H3F3O2, 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.

Propargyl amine (4.00 g, 72.62 mmol, 1.00 equiv.) was added dropwise to methyl trifluoroacetate (11.16 g, 87.15 mmol, 1.20 equiv.) at 0C. The reaction mixture was stirred at 0C for 2 h and then concentrated under reduced pressure to remove methanol. The product was purified by vacuum distillation yielding propargyltrifluoroacetamide as a colorless liquid (9.59 g, 87 %). The structure was confirmed by 1H- and 19F-NMR.

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

Reference:
Patent; Pierce Biotechnology, Inc.; Etienne, Christopher; Opperman, Kay; Kaboord, Barbara; Meier, Scott; Schultz, Jean-Samuel; EP2669291; (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. 251458-15-8, name is Methyl 2-(3-bromophenyl)-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-(3-bromophenyl)-2-methylpropanoate

A mixture of compound 21 b (319 mg, 0.7 mmol), methyl 2-(3-bromophenyl)-2-methyl- propanoate (203 mg, 0.8 mmol), Pd2(dba)3 (34 mg, 0.1 mmol), X-phos (86 mg, 0.2 mmol) and Cs2C03 (585 mg, 1.8 mmol) in toluene/.e/t-BuOH (30 mlJ5 mL) was heated to 110C overnight under N2. The mixture was cooled, filtered, concentrated and purified by FCC (PE:EA = 10:1) to give compound 21 as a yellow oil.

According to the analysis of related databases, 251458-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHENEX-FXR GMBH; GEGE, Christian; BIRKEL, Manfred; HAMBRUCH, Eva; DEUSCHLE, Ulrich; KREMOSER, Claus; (133 pag.)WO2018/188795; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2216-92-4, The chemical industry reduces the impact on the environment during synthesis 2216-92-4, name is N-Phenylglycine Ethyl Ester, I believe this compound will play a more active role in future production and life.

Example 35 1, 1-Dioxo-5-phenyl-1, 2, 5-thiadiazolidin-3-one sodium salt A. N-sulfamoylated-N-phenylglycine ethyl ester; A solution N-phenylglycine ethyl ester (1.0 g, 5.58 mmol) and TEA (1.69 g, 16. 7 mmol) in MeCN, 3mL is added dropwise to a freshly prepared solution of sulfamoyl chloride (5.58 mmol) in MeCN (5mL) over 20 min. The mixture is stirred at room temperature (RT) for 16 h. The solvent is evaporated and the residue is partitioned between EtOAc and water. The organic layer is dried over anhydrous sodium sulfate (Na2SO4) and evaporated. The residue is flash chromatographed on silica gel using 30% No. 50% EtOAc in hexanes as eluent to afford the N-sulfamoylated-N-phenylglycine ethyl ester as a yellow solid : [M+1] + = 259.

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, N-Phenylglycine Ethyl Ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2003/82841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.

[01289] Step 1 : Synthesis of methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-5-chloro- 2-methylbenzoate[01290] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 4.6 mmol) and tert-butyl (2-oxoethyl)carbamate ( 1 .4 g, 8.8 mmol) in methanol ( 10 mL), acetic acid (0.027 g, 4.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.352 g, 4.68 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired product (0.62 g, 38 %).

The synthetic route of 294190-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics