Esters-buliding-blocks

Related Products of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-isopropyl-5-(4-(6-(l,2,3,6-tetrahydropyridin-4- yl)benzo[d]thiazol-2-yloxy)piperidin-l-yl)-l,2,4-oxadiazole (Compound 43E, 95 mg, 0.223 mmol) and triethylamine (0.08 mL, 0.56 mmol) in CH2C12 (2mL) at 0 C was added methyl 3-(chlorosulfonyl)propanoate (62.5 mg, 0.335 mmol). The reaction mixture was stirred at 0 C for 15 min, then at rt overnight. The reaction mixture was quenched with sat. aq. aHC03 (2 mL) and extracted with CH2CI2 (3 x 3 mL). The combined organic layers were dried ( a2S04), filtered, and concentrated. The residue was purified by column chromatography (silica gel, CH2Cl2-EtOAc gradient 0 to 60% EtOAc) to afford methyl 3-(4-(2-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4- yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-l(2H)-ylsulfonyl)propanoate (75 mg, 0.13 mmol, 58% yield) as an off white solid. LCMS (m/z) =576 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-(chlorosulfonyl)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
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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 23062-51-3 as follows. Quality Control of Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate

Intermediate A51E: Methyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate To a suspension of aluminum trichloride (809 mg, 6.07 mmol) in benzene (4 mL, 1.214 mmol) at -10 C. was added a solution of Intermediate A51D (300 mg, 1.214 mmol) in benzene (2 mL) under nitrogen. The reaction mixture was gradually warmed up to RT and stirred overnight. It was carefully poured into ice water, extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51E (250 mg, 84%) as a tan solid, which was used for the next step without further purification. MS(ES): m/z=245 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 7.42-7.29 (m, 4H), 7.29-7.16 (m, 1H), 3.77-3.65 (s, 3H), 2.07-1.80 (m, 1H).

According to the analysis of related databases, 23062-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Electric Literature of 33842-16-9, 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. 33842-16-9 name is Methyl benzo[d][1,3]dioxole-4-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.

Method C; BenzoH ,31dioxole-4-carboxylic acidhydrazide (Intermediate compound); A mixture of 1 ,3-benzimidazole-4-carboxylic acid (3.0 g, 17,5 mmol), sulfuric acid (0.17 g, 1.75 mmol) and methanol (40 ml) was stirred at reflux for 15 h. The mixture of the intermediate benzo[1 ,3]dioxole-4-carboxylic acid methyl ester was allowed to reach room-temperature. Hydrazine monohydrate (8.5 g, 175 mmol) was added and the mixture was stirred at reflux for 15 h. The mixture was evaporated, water was added and the crystalline product was isolated by filtration. Yield 2.15 g (68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl benzo[d][1,3]dioxole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NeuroSearch A/S; PETERS, Dan; TIMMERMANN, Daniel, B.; NIELSEN, Elsebet, ?stergaard; DYHRING, Tino; CHRISTENSEN, Jeppe, Kejser; WO2010/86278; (2010); A1;,
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Electric Literature of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

2-(3-Fluorophenyl)acetohydrazide (2.90 g, 17.22 mmol) and ethyl 2-ethoxy-2- iminoacetate (2.5 g, 17.22 mmol) in ethanol (30 mL) was stirred under nitrogen at rt overnight. The resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound ethyl 2-amino-2-(2-(2-(3- fluorophenyl)acetyl)hydrazono)acetate (3 g, 11.23 mmol, 65.2 % yield), which was used without further purification. MS (m/z) 268 (M+H+).

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JEONG, Jae U.; KANG, Jianxing; LEISTER, Lara Kathryn; ROMANO, Joseph J.; (82 pag.)WO2018/7973; (2018); A2;,
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Synthetic Route of 106614-28-2,Some common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Methyl 2,4-difluorobenzoate (1.00 g; 5.81 mmol), 4-fluorophenol (0.72 g; 6.39 mmol) and potassium carbonate (1.61 g; 11.62 mmol) in DMF (20 mL) are stirred at 90C for 4 hours. The reaction mixture is diluted with water and extracted three times with DCM. The combined organic layers are dried over MgSC , filtered and concentrated under reduced pressure. The residue is purified by RP-HPLC (ACN/water + TFA). Yield: 0.45 g (29%) ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1.15 min (method 1)

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
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96999-01-8, name is Methyl 1-bromocyclopropanecarboxylate, 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. Computed Properties of C5H7BrO2

A mixture of 12j (2.40 g, 10 mmol), 3a-3b (15 mmol) andCs2CO3 (9.77 g, 30 mmol) in DMF (50 mL) was stirred at 90 C(for 3a) or 120 C (for 3b) in N2 atmosphere until the completion of reaction as indicated by TLC (typically within 12 h). Oncooling to room temperature, the reaction mixture was pouredinto ice-water (200 mL), and the mixture thus obtained wasextracted with CH2Cl2 (3 ¡Á 100 mL). The combined extractswere washed with 5% brine (5 ¡Á 100 mL), dried over anhydrous Na2SO4 and evaporated on a rotary evaporator to aord aresidue, which was purifed by column chromatography to yield21a-21b after trituration with EtOAc/n-hexane.6-Bromo-4-methylthioquinoline (21a). 1.07 g (42%). Whitesolid, m.p. 88-90 C. 1H NMR, delta 8.75 (d, J = 4.8 Hz, 1H),8.14 (d, J = 1.6 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.90 (dd,J = 2.0 Hz and 9.2 Hz, 1H), 7.40 (d, J = 4.8 Hz, 1H), 2.66(s, 3H). 13C NMR, delta 149.97, 146.97, 145.21, 132.71, 131.85,126.63, 124.88, 119.56, 116.27, 13.37. ESI-HR-MS, calcd. forC10H9BrNS ([M(79Br)+H]+) 253.9639, found 253.9641; calcd.for C10H9BrNS ([M(81Br)+H]+) 255.9619, found 255.9628.

The synthetic route of 96999-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Wang, Jianwu; Zhao, Guilong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 7; (2017); p. 799 – 811;,
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Application of 21597-54-6, The chemical industry reduces the impact on the environment during synthesis 21597-54-6, name is Methyl 3-amino-2-naphthoate, I believe this compound will play a more active role in future production and life.

40 g of compound A-1 (264 mmol) was added to a 500 ml three-necked flask, 16 g of formic acid and 160 ml of formamide were added, and the mixture was heated to 135 C for 5 h, and the reaction of the raw materials was completed by TLC; 200 ml of water was added, and the mixture was kept at 20 to 30 C for 1 h, and filtered. The filter cake was rinsed with water and recrystallized from ethanol to give 36.4 g of Compound A-2, yield 93.1%, purity 98.2%.

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-amino-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Jiu Mu Chemicals Co., Ltd.; Song Sisi; Chen Muxin; Li Xiangyang; Kong Xiangxing; Cui Lisha; (32 pag.)CN108178750; (2018); A;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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 57381-59-6, COA of Formula: C8H6BrFO2

Example 2bExample la (1748 mg, 77% content, 1 1 ,80 mmol) is added to sodium hydride (60% suspension in mineral oil, 472 mg, 1 1.80 mmol) in THF (5 mL). Stirring is continued at room temperature for 45 min. Methyl 5-bromo-2-fluorobenzoate (1 100 mg, 4.72 mmol) in THF (5 mL) is added and stirring is continued at room temperature overnight. Example la (65 mg, 75% content, 0.43 mmol) is added to sodium hydride (60% suspension in mineral oil, 17 mg, 0.43 mmol) in THF (1 mL) and the resulting mixture added to the reaction mixture and stirring is continued at room temperature overnight. The reaction mixture is diluted with DCM, washed with saturated NH4CI, dried and concentrated under reduced pressure giving a residue. Trimethylsilyldiazomethane in hexanes (2M, 2.153 mL, 4.3 mmol) is added dropwise to the residue in DCM (5 mL) and MeOH (2.5 mL) cooled to 0C. Stirring is continued for 120 min, then the reaction mixture is evaporated under reduced pressure to furnish the title compound (200 mg, 50%> content, 7%>).HPLC-MS (Method 2): Rt = 1.38 minMS (ESI pos): m/z = 327 (M+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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
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Ester – an overview | ScienceDirect Topics

Reference of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

Tert-butyl(chloro)diphenylsilane (18 ml, 68 mmol, CAS No 58479-61-1 ) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, CAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, CAS No 16681-56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, CAS No 1 122-58-3) in dimethylformamid (81 ml), and the mixture was stirred at room temperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5percent -> 30percent ethyl acetate) to give the title compound (21 g)

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Safety of tert-Butyl 4-bromobutanoate

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1.15 g, 6.87 mmol) and Cs2CO3 (13.43 g, 41.2 mmol) in DMF (45 mL) is stirred at rt for 30 min before tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added. The orange suspension is stirred at 65 C. for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added and stirring is continued at 65 C. for 24 h. The mixture is dilued with water (150 mL) and extracted three times with DCM (3*50 mL) and EA (3*50 mL). The org. extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR=1.01 min, [M+H]+=no mass detectable; 1H NMR (D6-DMSO): delta 7.94 (d, J=1.7 Hz, 1H), 7.75 (d, J=1.3 Hz, 1H), 3.95 (t, J=6.3 Hz, 2H), 2.46 (t, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.98 (quint, J=6.6 Hz, 2H), 1.41 (s, 9H).

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Morrison, Keith; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2013/303514; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics