Month: August 2021

Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Step 1; 4-(l-terf-Butoxycarbonyl-cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester: To a cooled (-780C) solution of 2.OM lithium dsopropylamide in heptane/ THF/ ethylbenzene (27.4 mL, 54.8 mmol) was added cyclopropanecarboxylic acid terf-butyl ester (7.08 g, 49.8 mmol) in THF (35 mL). After stirring at -780C for 1 h, a solution of 4-oxo-piperidine-l- carboxylic acid benzyl ester (11.6 g, 49.8 mmol) in THF (50 mL) was added. The reaction mixture was stirred at -780C for 3 h then warmed to room temperature. After stirring at ambient temperature for 16 h, the mixture was quenched with saturated aqueous solution of NH4Cl (150 mL) and extracted with EtOAc (150 mL x 3). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc in Hexane) to yield 4-(l-tert-butoxycarbonyl- cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester (8.07 g, 43%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.28 (m, 5H), 5.11 (s, 2H), 4.50 (s, IH), 4.00 (bis, 2H), 3.20 (brs, 2H), 1.72- 1.64 (m, 2H), 1.42 (s, 9H), 1.40-1.30 (m, 2H), 1.10 (dd, J=7.0 and 2.4 Hz, 2H), 0.88 (dd, J=7.0 and 2.4 Hz, 2H).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; PETERSON, John; CHEN, Chien-an; CHEN, Bin; WU, Lingyun; SABIO, Michael; WO2010/53861; (2010); A2;,
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These common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, 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. Formula: C9H10FNO2

To a stirred solution of [3-(1, 1-DIMETHYLETHYL)-1-ETHYL-4, 5-DIHYDRO-LH-PYRAZOLE-] 5-carboxylic acid (i. e. the product of Step D) (0.8 g, 4.1 mmol) in dichloromethane (5 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt % solution in ethyl acetate, 3.9 g, 6.14 mmol) followed by 4- (dimethylamino) pyridine [(0. 75] g, 6.14 mmol). After stirring for 1 h, ethyl [3-AMINO-4-FLUOROBENZOATE] (0.68 g, 3.7 mmol) was added, and the resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo and partitioned between water (50 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (30 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (50 mL) and water (50 mL), and dried [(MGSO4).] The solvent was removed in vacuo to provide the title product, a compound of the present invention, as an oil (1.36 g). 1H NMR (CDC13): [B] 9.3 (s, 1H), 8.95 (d, 1H), 7.80 (m, 1H), 7.16 (t, 1H), 3.70 (t, 1H), 3.33 (dd, 1H), 3.18 (dq, 1H), 2.95 (dq, 1H), 2.83 (dd, 1H), 1.39 (t, 3H), 1.21 (t, 3H), 1.17 (s, 9H).

The synthetic route of Ethyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; WO2004/35545; (2004); A2;,
Ester – Wikipedia,
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Application of 31930-34-4,Some common heterocyclic compound, 31930-34-4, name is Ethyl cis-3-Bromoacrylate, molecular formula is C5H7BrO2, 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.

In a round-bottomed flask, at 0 C,were successively added Et3N (45 mL), F (5.25 g, 29 mmol), triisopropylsilylacetylene(6.5 mL, 29 mmol), PdCl2(PPh3)2 (330 mg, 0.5 mmol) and CuI (95 mg, 0.5 mmol). The mixture was stirred at 0 C for 4 h, then water (50 mL) was added. The crude was extracted with EtOAc(2 × 50 mL), washed with brine, dried over Na2SO4, filtered and concentrated in vacuum. After purification by chromatography on silica gel (cyclohexane/ethyl acetate 98:2), 6.6 g of an orange liquid were obtained (81% yield). 1H NMR (300 MHz, CDCl3) delta 6.14 (d, J = 11.7 Hz,1H), 6.05 (d, J = 11.7 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 1.27 (t, J = 7.1 Hz, 3H), 0.80-1.50 (m,21H). 13C NMR (126 MHz, CDCl3) delta 164.6, 129.4, 122.4, 105.1, 102.6, 60.5, 18.7, 14.4, 11.5. HRMS (ESI-TOF) m/z [M + Na]+ Calcd for C16H28NaO2Si 303.1751; Found 303.1764.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl cis-3-Bromoacrylate, its application will become more common.

Reference:
Article; Fuentespina, Ruben Pomar; De La Cruz, Jose Angel Garcia; Durin, Gabriel; Mamane, Victor; Weibel, Jean-Marc; Pale, Patrick; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1416 – 1424;,
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105-53-3, name is Diethyl malonate, 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. Recommanded Product: 105-53-3

The compound 1,1,1-triethoxyethane (62.6 mL, 341 mmol),Compound diethyl malonate (224.4 mL, 990.1 mmol),Acetic anhydride (1.4 mL, 10.1 mmol) and a catalytic amount of zinc chloride (0.1 g) were placed in a reaction flask and heated to 170 C for 5.0 h.Evaporating unreacted diethyl malonate under reduced pressure,The residue was purified by column (eluent: PE/EtOAc (v/v) = 20/1).40.0 g of yellow oil were obtained.The yield was 69.8%.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Liu Bing; Liu Jinlei; Zhang Yingjun; Zhang Jiancun; (158 pag.)CN104744446; (2019); B;,
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Synthetic Route of 35450-37-4, 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. 35450-37-4, name is Methyl 3-bromo-4-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 To a 250 mL RBF was added methyl 3-bromo-4-methoxybenzoate (4.0 g, 16.3 mmol). The flask was flushed with N2. THF (60 mL) was added, followed by allylmagnesium bromide (39.2 mL, 39.2 mmol, 1.0 M in ether) at 0 C. via a syringe over 10 mins. The resulting reaction mixture was stirred at 0 C. for 2 hrs. It was quenched by addition of 50 mL sat. NH4Cl at 0 C. and 100 mL of water. The product was extracted with EtOAc (3*100 mL). Organics were washed with 100 mL brine, dried over sodium sulfate, filtered, and concentrated to give 4-(3-bromo-4-methoxyphenyl)hepta-1,6-dien-4-ol (5.0 g) as a colorless oil. 1H NMR (500 MHz, CDCl3:) delta 7.61 (s, 1H), 7.30 (d, 1H), 6.88 (d, 1H), 5.63 (m, 2H), 5.12 (d, 4H), 3.93 (s, 3H), 2.65 (m, 2H), 2.53 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-4-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 4934-99-0, Recommanded Product: 4934-99-0

To a solution of methyl 3-hydroxycyclobutanecarboxylate AA28 (19.7 g, 152 mmol) in dichloromethane (200 mL) was added pyridine (90.0 g, 1.14 mol) , 4-dimethylaminopyridine (5.60 g, 45.6 mmol) and tosyl chloride (58.0 g, 303 mmol) at room temperature. After stirred at room temperature overnight, the mixture was poured water (200 mL) and extracted with ethyl ester (200 mL) twice. The combined organic layers were washed with 0.5 M hydrochloride aqueous solution (200 mL) , saturated sodium bicarbonate aqueous solution (200 mL) , water (200 mL) and brine (200 mL) , dried over Na2SO4 (s), filtered and the filtrate was concentrated under reduced pressure at room temperature to afford the title compound (42.7 g, 99 %yield) as yellow oil.1H NMR (300 MHz, CDCl3) delta 7.77 -7.73 (m, 2H) , 7.34 -7.26 (m, 2H) , 4.77 -4.64 (m, 1H) , 3.66 -3.59 (m, 3H) , 2.67 -2.54 (m, 1H) , 2.50 -2.37 (m, 7H) .

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

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; JIANG, Yimin; WAN, Zhao-Kui; CHEUNG, Wing Shun; LIU, Qian; DENG, Gang; LIANG, Chao; (230 pag.)WO2019/214610; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, 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 150529-73-0, Product Details of 150529-73-0

(The following reaction is done in an oxygenfree N2 atmosphere.) Add ethanol (0.8mL), Tetrakis-(triphenylphosphine)-palladium(0) (30mg, 2.2mol%) and Na2CO3 decahydrate (944mg, 3.30mmol; presolved in 1.2mL H2O) subsequently to dissolved 2-Amino-benzeneboronic acid (48) (201mg, 1.30 mmol) in toluene (6.0mL). Degas the reaction mixture for 5 times and flood with N2 again. Add (3-Bromo-phenyl)-acetic acid methyl ester (47) (270mg, 1.18mmol) in toluene (6.0 mL), degas again (5 times) and stir the reaction solution overnight at 100C. Partition the reaction solution between EtOAc and brine (1+1) and extract the separated aqueous layer 3 times with EtOAc. Wash combined organic layer with brine and dry with Na2SO4. Remove solvent under reduced pressure and purify the crude product by preparative radial chromatography (silica gel 60PF, CyH/EtOAc 3+1) to obtain (2′-Amino-biphenyl-3-yl)-acetic acid methyl ester (49) as an orange oil (304mg, 81%). 1H NMR (400MHz, CDCl3): 3.66 (s, 2 H); 3.69 (s, 3 H); 3.62-3.86 (br.s, 2 H); 6.75 (d, 1 H, J= 8.1Hz); 6.80 (t, 1 H, J= 7.3Hz); 7.11 (d, 1 H, J= 7.3Hz); 7.15 (d, 1 H, J = 8.1Hz); 7.22-7.26 (br.m, 1 H); 7.32-7.42 (m, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3-bromophenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Revotar Biopharmaceuticals AG; EP1764093; (2007); 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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Step A:; The imidate salt 1g2(1.4 g, 7.2 mmol, 1 eq.) was combined with 2-(methylthio)aniline 111 (0.96 g, 7.50 mmol, 1 eq.) in ethanol (15 mL) under an N2atmosphere. The reaction mixture was stirred at RT (1 h) and monitored by HPLC.The reaction mixture was concentrated and then ether was added and the mixturefiltered. The solids were washed with ether and the combined ether washesconcentrated in vacua. The resulting adduct 112 was obtained as a yellow oil (1.66 g,82percent) and used as is in the next step. MS electrospray: (M + H)+; 282 and (M – H)”;280.

The synthetic route of 2318-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/7700; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 42726-73-8 as follows. Recommanded Product: tert-Butyl methyl malonate

Example 143B 1-tert-butyl 3-methyl 2-(6-ethoxy-5-nitropyridin-2-yl)malonate To a solution of Example 143A, 6-chloro-2-ethoxy-3-nitropyridine (3 g, 14.81 mmol), in N,N-dimethylformamide (30 mL) at 0° C. was added sodium hydride (1.185 g, 29.6 mmol), and the mixture was stirred for 20 minutes. Then, tert-butyl methyl malonate (3.16 mL, 17.77 mmol) was added dropwise, and the mixture was stirred at ambient temperature for 2 hours. The mixture was diluted with ether and quenched with H2O. The mixture was partitioned. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel eluting with 0-20percent ethyl acetate/heptanes to provide the titled compound.

According to the analysis of related databases, 42726-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie Inc.; Altenbach, Robert J.; Liu, Huaqing; Clapham, Bruce; Aguirre, Ana L.; Cowart, Marlon; Koenig, John R.; Sarris, Kathy; Scanio, Marc J.; Swinger, Kerren K.; Vasudevan, Anil; Villamil, Clara I.; Woller, Kevin R.; (95 pag.)US9777020; (2017); B2;,
Ester – Wikipedia,
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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. 121-98-2, name is Methyl 4-methoxybenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H10O3

General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 mol%), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 mum and RTX-wax 30 m × 25 mum) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200-300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC-MS or GCD, which are consistent with those reported in the literature.

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:
Conference Paper; Liu, An-Hua; Ma, Ran; Zhang, Meng; He, Liang-Nian; Catalysis Today; vol. 194; 1; (2012); p. 38 – 43;,
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Ester – an overview | ScienceDirect Topics