Category: esters-buliding-blocks

Some common heterocyclic compound, 175867-59-1, name is Methyl 4-aminocyclohexanecarboxylate, molecular formula is C8H15NO2, 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. COA of Formula: C8H15NO2

EXAMPLE 23(1) 2-[4-(Methoxycarbonyl)cyclohexylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (381 mg) was obtained from 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (300 mg) and methyl 4-amino-1-cyclohexanecarboxylate (222 mg) in a manner similar to Example 1(1). NMR (CDCl3, delta): 1.70-2.03 (8H, br), 2.52 (1H, br), 3.63 (1H, br), 3.71 (3H, s), 4.50 (2H, d, J=7 Hz), 5.97 (2H, s), 6.41 (1H, br), 6.66 (1H, m), 6.78-6.87 (3H, m), 8.14 (1H, m), 8.30 (1H, m), 8.86 and 9.08 (1H, br); Mass m/z: 456(M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175867-59-1, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6384080; (2002); B1;,
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Reference of 94994-15-7, These common heterocyclic compound, 94994-15-7, name is Methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, 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 a solution of 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (108 mg, 0.545 mmol), methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-l-carboxylate (90 mg, 0.454 mmol) and triphenylphosphine (179 mg, 0.681 mmol) in toluene (2 mL) at 0 C was added (¡ê)-di-tert-butyl diazene-l,2-dicarboxylate (157 mg, 0.681 mmol) in toluene (0.5 mL) slowly. The reaction mixture was stirred at room temperature for 5 min and the reaction mixture was heated to 90 C for 18 hours. After cooled to room temperature, dichloromethane (5 mL) and water (5 mL) were added to the reaction mixture. The layers were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated in vacuo to afford the crude. This crude was purified by preparative HPLC (PHENOMENEX Axia 5 muiotaeta C18 30 x 100 mm column; detection at 220 nm; flow rate = 40 mL/min; continuous gradient from 30% B to 100% B over 10 min + 5 min hold time at 100% B, where A = 90: 10:0.1 H20:MeOH:TFA and B = 90: 10:0.1 MeOH:H20:TFA) to give the title compound (75 mg, 41.5% Yield; 95% pure by LC/MS) as a light yellow oil. [M+Na]+ = 401, pi MR (400 MHz, CDC13) delta 6.70 (dd, J= 14.3, 1.6 Hz, 2H), 3.65 (s, 3H), 3.63 (s, 2H), 2.96 (s, 2H), 1.86 – 1.77 (m, 6H), 1.59 – 1.55 (m, 6H), 1.48 (s, 6H).

The synthetic route of 94994-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; ZHANG, Hao; CHENG, Peter T.W.; TAO, Shiwei; WO2014/159802; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 49851-36-7,Some common heterocyclic compound, 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, molecular formula is C9H12ClNO2, 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.

TEA (0.324 mL, 2.325 mmol) was added to a mixture of 3-acetamido-5-bromobenzoic acid (CAS 78238-1 1 -6) (200 mg, 0.775 mmol) and HATU (324 mg, 0.852 mmol) in DMF (3 mL) at 23 C. After 5 min, methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (165 mg, 0.775 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was partitioned between 4: 1 EtOAc/heptanes and water. The aqueous layer was extracted with 4: 1 EtOAc/heptanes. The combined organic layers were washed with 5% aqueous LiCI solution, the organics were dried (Na2S04), filtered and concentrated. The residue was purified by silica gel chromatography (EtOAc/heptanes 20-80%) to provide the title compound. MS (ESI+) m/z 405.2, 407.2 (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 Methyl 2-(2-aminophenyl)acetate hydrochloride, its application will become more common.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 758684-29-6, name is Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, 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 758684-29-6, Computed Properties of C10H11NO3

Benzenesulfonyl chloride (43.9 mg, 0.248 mmol) and N,N-diisopropylethylamine (0.108 mL, 0.621 mmol) were added to a solution of methyl 3,4-dihydro-2H- benzo[b][l,4]oxazine-6-carboxylate (40 mg, 0.207 mmol) in acetonitrile (2 mL), and the reaction stirred at ambient temperature overnight. The reaction was diluted with ethyl acetate and washed with brine. The organic phase was separated and concentrated to afford methyl 4- (phenylsulfonyl)-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate which was used directly in the next step without further purification. MS: (ES, m/z): 366 [M+S+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, Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

Application of 426-65-3, 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. 426-65-3, name is Ethyl Pentafluoropropionate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of alkyne (1.0 eq) in THF (0.5 M) was added dropwise n-BuLi in solution in hexanes (1.1 eq) at -78 C. The mixture was stirred for 1 h at -78 C and ethyl trifluoroacetate (1.5 eq) was added. After the complete consumption of the alkyne (TLC), the mixture was diluted with MeOH (same volume than THF). The mixture was allowed to warm up to 0 C and NaBH4 (1.0 eq) was added. The mixture was stirred overnight while warming up to room temperature. The reaction was then quenched with a saturated solution of NH4Cl, extracted with Et2O (x3), washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give the alpha-trifluoromethyl secondary propargylic alcohol. The crude product was purified by flash column chromatography to afford the pure product.

The chemical industry reduces the impact on the environment during synthesis Ethyl Pentafluoropropionate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Boreux, Arnaud; Lambion, Aubin; Campeau, Dominic; Sanita, Marina; Coronel, Ruben; Riant, Olivier; Gagosz, Fabien; Tetrahedron; vol. 74; 38; (2018); p. 5232 – 5239;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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 3697-68-5, Formula: C7H12O3

To a solution of ethyl 1 -(hydroxymethyl)cyclopropanecarboxylate (2.0 g, 13.87 mmol) in DCM (25 mL) was added trichloroisocyanuric acid (3.26 g, 14.01 mmol) and followed by TEMPO (0.217 g, 1.387 mmol) at-S C. The reactionmixture was stirred for 1 h at -S C. The mixture was filtered through celite, and diluted with DCM (SO mL). The solution was washed with saturated Na2CO3 (SO mL), iN HC1 (SO mL), brine (SO mL), and saturated NH4C1 (3xSO mL). The organic layer was dried over Na2504, filtered, and concentrated under reduced pressure to obtain ethyl 1-formylcyclopropanecarboxylate (1.5 g, 10.55 mmol, 76 % yield) ascolorless liquid; product was used for next step without purification. ?H NMR (CDC13, oe = 7.26 ppm, 300 MHz): oe 10.40 (s, 1 H), 4.28 (q, J= 7.1 Hz, 2 H), 1.72 – 1.56 (m, 4 H), 1.32 (t, J= 7.1 Hz, 3 H).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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Ester – an overview | ScienceDirect Topics

Reference of 23426-63-3, 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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-PYRIDIN-3-YL-PHENOL (0.86 g, 5.0 mmol), methyl 2- bromoisobutyrate (3.60 g, 20.0 MMOL), and K2CO3 (2.76 g, 20.0 mmol) in anhydrous DMF (10 mL) was heated at 93 C under nitrogen for 3 h. After cooling, brine (40 mL) was added and the mixture was extracted with ethyl acetate (50 mL). The separated organic layer was washed with brine, filtered, and concentrated. The oil residue was taken up in 10 mL of 3 M HCI, stirred for 10 min, diluted with brine (10 mL), and extracted with ethyl acetate (2 x 30 mL). The separated aqueous layer was cooled in ice/water bath, adjusted to pH 10 with solid NA2CO3, and extracted with ethyl acetate (2 x 40 mL). The organic extract was dried over sodium sulfate and concentrated to afford 1.09 g (80%) of 2-METHYL-2- (3-PYRIDIN-3-YL-PHENOXY)-PROPIONIC acid methyl ester as a yellow oil :’H NMR (CD3) 6 1.62 (s, 6H), 3.79 (s, 3H), 6.82 (dd, 1 H), 7.08 (s, 1 H), 7.20 (d, 1 H), 7.38 (m, 2H), 7.81 (d, 1 H), 8.59 (d, 1 H), 8.80 (s, 1 H) ; MS M/Z (relative intensity) 271 (M+, 20), 212 (30), 171 (100).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-2-methylpropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/48334; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 34846-90-7, name is Methyl 3-methoxyacrylate, A new synthetic method of this compound is introduced below., Product Details of 34846-90-7

1.70 g (10 mmol) of 4-cyanophenylhydrazine hydrochloride, 1.16 g (10 mmol) of methoxypropan-2-ol were added to a three-necked reaction flaskMethylene chloride, 10 mL of methanol. The temperature of the reaction mixture was raised to reflux for about 6 hours. The reaction solution was quantitated by liquid chromatography, and 1- (4-cyanoPhenyl) -5-hydroxypyrazole Yield 64.2percent

The synthetic route of 34846-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan Haili Changde Agrochemical Co.,Ltd.; Hu, Zhibin; Liu, Weidong; Du, Shenghua; Huang, Chaoqun; Lan, Shilin; Xiong, Lili; Wu, Yinyin; Cheng, Chao; Wang, Yanli; (6 pag.)CN104059020; (2016); B;,
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Ester – an overview | ScienceDirect Topics

Reference of 25662-28-6, 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. 25662-28-6 name is Methyl 1-cyclopentene-1-carboxylate, 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.

Experimental Procedures-Part 1 :; Step 1 – Oxidation of Carboxymethylcyclopentene:; Procedure:; To a cooled (00C) 2 L round bottom flask with a magnetic stir bar and internal temperature probe was added acetic anhydride (615 g, 570 mL, 6.02 mol). Chromium trioxide (214 g, 2.14 mol) was added in portions while maintaining constant stirring and to control the exotherm. The resulting blood red solution was stirred to dissolve the chromium trioxide until the temperature had cooled to 20 0C. A 5 L three-neck flask was fitted with an addition funnel, overhead stirring mechanism, nitrogen inlet and internal temperature probe and charged with 4 (100 g, 101 mL, 0.793 mol) in 1.4 L CH2Cl2. The oxidizing solution of chromium trioxide and acetic anhydride was charged to the addition funnel and added dropwise to the reaction mixture, maintaining the internal temperature between 10 and 14 0C. The initially yellow solution became dark after the first few drops of oxidizer were added.The reaction was worked up in two equally-sized batches due to limitations on vessel size in the laboratory. Each batch was treated exactly the same way, as follows: The dark, homogeneous solution was poured carefully into a 4 L beaker with an overhead stirring mechanism. The reaction flask was rinsed with 250 mL CH2Cl2. 500 mL H2O was added followed by 10 g NaHCC?3 which resulted in gas evolution. Additional NaHCC>3 (830 g, 10 mol) was added in portions while maintaining 500 rpm stir rate in the viscous mixture. The resulting dark green suspension was diluted with 1 L H2O and filtered through a 3 L fritted funnel containing a 1 cm pad of solka floe. The biphasic solution was extracted with CH2CI2 (3×1 L) and the combined organics dried using MgSO.), then filtered and the resulting solution was concentrated in vacuo to afford a pale green oil. Distillation through a 30 cm Vigreux column followed by recrystallization from MTBE:hexane (1:10, 55 mL total) provided 38.4 g of 5 as a white crystalline solid (35%).ted yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-cyclopentene-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; BANYU PHARMACEUTICAL CO., LTD.; WO2008/21029; (2008); A2;,
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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H13BrO2

A.i. (RS)-tert-Butyl 2-(methylsulfonyl)propanoate : To a suspension of sodium methanesulfinate (100 g; 929 mmol) in tBuOH (350 mL) was added iert-butyl-2-bromopropionate (150 mL; 877 mmol). The reaction mixture was stirred at 90C for 24 h under nitrogen atmosphere, then cooled to rt and concentrated to dryness. The residue was partitioned between water (750 mL) and EA (600 mL). The aq. layer was extracted with EA (2 x 500 mL). The evaporation residue afforded the title compound as a white yellow solid (175 g; 96% yield). 1H NMR (DMSO-d6) delta: 4.24 (q, J = 7.2 Hz, 1H); 3.1 1 (s, 3H); 1.45 (s, 9H); 1.40 (d, J = 7.2 Hz, 3H).

According to the analysis of related databases, 39149-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DIETHELM, Stefan; GAUVIN, Jean-Christophe; JACOB, Loic; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; TIDTEN-LUKSCH, Naomi; (79 pag.)WO2019/86452; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics