Tag: M.W=100-200

Reference of 17205-02-6, 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. 17205-02-6 name is Ethyl 3-hydroxycyclobutanecarboxylate, 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.

[0729] To a solution of ethyl 3-hydroxycyclobutanecarboxylate (10.2 g, 78.4 mmol) in dry pyridine (56.5 mL) at ooC., TsCI (14.9 g, 78.4 mmol) was added portionwise. Theresulting mixture was stirred at rt overnight. The reactionmixture was concentrated under reduced pressure and theresidue obtained was dissolved in EtOAc (100 mL) andsequentially washed with 2 N HCI (100 mL), saturatedNaHC03 (100mL)andwater(100mL). TheEtOAclayerwasdried over Na2S04 , filtered, and concentrated to obtain ethyl3-(tosyloxy)cyclobutanecarboxylate as a pale yellow oil,which was used in the next step without further purification.[0730] To a solution ethyl 3-(tosyloxy)cyclobutanecarboxylate (6.0 g, 20 mmol, as prepared above) in anhydrousMEK(20mL), Nal (7.5 g, 50mmol)was added. Theresultingmixture was heated at 120 C. for 4 h in a microwave reactor.The reaction mixture was concentrated and water (50 mL)was added. The resultant mixture was extracted with ether(100mL) and washed with 10% Na2 S 20 3 (50mL) and water(50 mL). The ether layer was separated, dried over Na2S04 ,filtered, and concentrated. The residue was distilled underreduced pressure to obtainthe title compound 43a as a cis andtrans mixture. 1 H-NMR (400 MHz, CDCI 3 ) o (ppm): 4.66(quin, 1=7.2 Hz, lH), 4.30-4.48 (m, 2H), 4.02-4.24 (m, 6H),3.30-3.49 (m, lH), 3.03-3.21 (m, 2H), 2.64-3.02 (m, 12H),1.18-1.34 (m, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-hydroxycyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); 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 18595-18-1 as follows. SDS of cas: 18595-18-1

To a solution of 6,7-bis-(2-methoxy-ethoxy)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (0.1 g, 0.30 mmol) in DMF (5 mL) was added HATU (0.137 g, 0.36 mmol) (Aldrich), triethylamine (0.1 mL, 0.72 mmol) (Fluka) and 3-amino-4-methyl-benzoic acid methyl ester (0.059 g, 0.36 mmol) (TCI). The reaction mixture was stirred at room temperature for 18 hours. Then, water (5 mL), saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate (10 mL) were added. After mixing, the precipitate was filtered under vacuum and washed with ethyl acetate. The resulting solid was dried under air to provide 3-{[6,7-bis-(2-methoxy-ethoxy)-2-oxo-1,2-dihydro-quinoline-3-carbonyl]-amino}-4-methyl-benzoic acid methyl ester(1-phenyl-propyl)-amide. (Yield 0.064 g, 55%). HR-MS (ES+) m/z Calculated for C25H29N2O8 ([M+H]+): 485.1919. Found: 485.1919.

According to the analysis of related databases, 18595-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dominique, Romyr; Luk, Kin-Chun; Qiao, Qi; Rossman, Pamela Loreen; US2012/184548; (2012); A1;,
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These common heterocyclic compound, 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, 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. Computed Properties of C7H12O3

Description 52Ethyl 3-(tosyloxy)cyclobutanecarboxylate (D52)TsOTo a solution of ethyl 3-hydroxycyclobutanecarboxylate (800 mg) in DCM (40 mL) was added TsC1 (1.14 g) and pyridine (0.898 mL) at RT. The mixture was then stirred at RT overnight. The mixture was washed with water (2×20 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum to leave the crude as yellow oil, which was purified byflash chromatography (silica gel, petroleum ether/EtOAc = 20:1) to afford the title compound (600mg) as colorless oil. MS (ESI): C14H1805S requires 298; found 299 [M+H].

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; LIN, Xichen; WO2015/180612; (2015); 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. 61644-18-6, name is Chloromethyl isobutyrate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Chloromethyl isobutyrate

Example 2 Preparation of 2-((3S,7R,8R,9S)-8-(isobutyryloxy)-3-(3-(isobutyryloxymethoxy)-4-methoxypicolinamido)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)ethyl benzoate (Compound 19) To a mixture of 2-((3S,7R,8R,9S)-3-(3-hydroxy-4-methoxypicolinamido)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)ethyl benzoate (50 mg, 0.087 mmol), Na2CO3 (15 mg, 0.14 mmol) and NaI (3.09 mg, 0.021 mmol) in acetone (0.6 mL) was added chloromethyl isobutyrate (15.4 mg, 0.114 mmol) slowly at room temperature (about 22 C.). The resulting reaction mixture was warmed to 50 C. and stirred at 50 C. overnight. The solvent was evaporated and the crude residue was purified via flash chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (35 mg, 76%) as an off-white solid: mp 48-50 C.; 1H NMR (300 MHz, CDCl3) delta 8.55 (d, J=7.9 Hz, 1H), 8.26 (d, J=5.5 Hz, 1H), 8.04-7.87 (m, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.95 (d, J=5.4 Hz, 1H), 5.85-5.62 (m, 2H), 5.41 (s, 1H), 5.26-5.06 (m, 2H), 4.94 (dd, J=9.8, 6.3 Hz, 1H), 4.42-4.19 (m, 2H), 3.92 (d, J=14.3 Hz, 3H), 3.65 (s, 1H), 2.76 (t, J=9.5 Hz, 1H), 2.62 (dt, J=10.8, 5.5 Hz, 1H), 2.58-2.47 (m, 1H), 2.30 (s, 1H), 1.82 (s, 1H), 1.29 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 0.9 Hz, 6H), 1.13 (d, J=7.0 Hz, 6H); ESIMS m/z 673 ([M+H]+).

According to the analysis of related databases, 61644-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Meyer, Kevin G.; Li, Fangzheng; Renga, James M.; Owen, W. John; Nugent, Benjamin M.; Yao, Chenglin; Wang, Nick X.; US2013/296371; (2013); 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. 2005-10-9, name is 6H-Benzo[c]chromen-6-one, A new synthetic method of this compound is introduced below., Formula: C13H8O2

Magnesium (0.190 g, 7.50 mmol) was placed into an oven-dried round bottom flask and flushed with Ar for 30 min while stirring. 4-Bromobiphenyl 5 (1.75 g, 7.50 mmol), anhydrous THF (10 mL), and a crystal of I2 were then added and the reaction stirred for 1.5 h under Ar. During this time 6H-benzo[c]chromen-6-one 9 (0.981 g, 5.00 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The flask was cooled to 0 C with an ice bath and sparged for 30 min with Ar. The arylmagnesium bromide solution was transferred to the solution containing 9 at 0 Cvia cannula under Ar pressure. The cooling bath was removed, and the reaction was stirred for 18 h. 50 mL of sat. NH4Cl was added to the reaction and subsequently extracted 3x with 25 mL of Et2O. The combined organics were dried with Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in25 mL of diethyl ether and cooled to 0 C in an ice bath and stirred very rapidly. A chilled (0 C) solution of 70% perchloric acid in acetic anhydride (1:3 by volume) was slowly added drop-wise to the stirring ethereal solution until a colored precipitate formed. The crude product was filtered and recrystallized in glacial acetic acid to yield orange-yellow needles (1.36 g, 63%). mp 234e236 C. 1H NMR(400 MHz, CDCl3/CF3CO2D): d 8.93 (d, J 8.3 Hz, 1H), 8.87 (d,J 8.3 Hz, 1H), 8.79 (d, J 8.3 Hz, 1H), 8.61 (t, J 8.3 Hz, 1H), 8.36(d, J 8.5 Hz, 2H), 8.29 (d, J 8.5 Hz, 1H), 8.20-8.04 (m, 5H), 7.80-7.77 (m, 2H), 7.61-7.52 (m, 3H). 13C NMR (100 MHz, CDCl3/CF3CO2D): d 183.8, 151.5, 150.0, 143.9, 139.6, 138.1, 136.2, 134.6,134.2, 132.0, 130.8, 129.8, 129.4, 128.6, 127.9, 127.6, 123.1, 123.9,121.5, 120.6, 119.9. IR (ATR) nmax: 1597, 1542, 1069 cm1. HRMS (ESI)m/z calcd for C25H17O [M] 333.1279, found 333.1276.

The synthetic route of 2005-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J.; Tetrahedron; vol. 76; 23; (2020);,
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Related Products of 2901-13-5, These common heterocyclic compound, 2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate, 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.

Example 2: Synthesis of 2-(4-(chloroacetyl)phenyl)-2-methylpropionic acid ethyl esterIn a 5L reaction flask, add 2,2-dimethylphenylacetic acid ethyl ester (542g, 2.8mol), 2L dichloromethane solution. Stir. Add anhydrous aluminum chloride (600g, 4.5mol), then add dropwise a chloroacetyl chloride (318.6g,2.8mol) in 500mL of methylene chloride mixture. After reacting for a period,detection by TLC finish the reaction was stopped, the organic layer was separated, and the organic layer washed with water, saturated sodium bicarbonate solution , washed with saturated sodium chloride solution, dried and concentrated to give 2-(4-(chloroacetyl)phenyl)-2-methylpropionic acid ethyl ester (660g, 87%).

The synthetic route of 2901-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Huawe Medicine Technology Development Co., Ltd.; Xu, Feng; Hu, Dandan; Huang, Hui; Jiang, Yuwei; Zhang, Xiaoqing; (6 pag.)CN104276952; (2016); B;,
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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 4630-82-4 as follows. Computed Properties of C8H14O2

Example 5; Catalytic hydrogenation of various esters using complex [RuCyT?-BINAP)(S,S-DPEN)]; General procedure for the catalytic hydrogenation of methyl benzoate as substrate: Under argon, a Keim autoclave was charged with [RuCl2(i?-BINAP)(dmf)2] (0.01 mmol, 0.05 mol%) and S5S-DPEN (0.01 mmol, 0.05 mol%) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2 x 1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2 x 1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol%) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 600C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.Table 5 : Hydrogenation of various esters using complex [RuCl^-BINAPX^S-DPEN)]Com/Base: molar ratio in ppm relative to the substrate of complex and base. GC: percent of product analysed by GC in the crude reaction mixture. Reaction conditions: H2 gas (50 bars), 600C, NaOMe as base and THF (2 M).

According to the analysis of related databases, 4630-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FIRMENICH SA; WO2008/65588; (2008); A1;,
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These common heterocyclic compound, 52273-79-7, name is Ethyl 2-(3-aminophenyl)acetate, 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: C10H13NO2

(3-Amino-phenyl)-acetic acid ethyl ester (0.895 g, 5.0 mmol) and acetyl chloride (0.26 mL, 5.0 mmol) are added to a round bottomed flask containing THF (20 mL), pyridine (0.60 mL) and DMAP (10 mg). The mixture is stirred at room temperature overnight. The clear solution is diluted with EtOAc (200 mL), washed with 1N HCl (3¡Á100 mL) and brine (100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford intermediate 14-B as a white solid that is used without further purification

The synthetic route of Ethyl 2-(3-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; US2007/276002; (2007); A1;,
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Related Products of 369-25-5,Some common heterocyclic compound, 369-25-5, name is Methyl 3,4-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.

Intermediate 9: Methyl 4-{(3S)-aminopiperidin-1-yl}-3-fluorobenzoate N -Methylpyrrolidone (40 ml) was added to methyl 3,4-difluorobenzoate (1.29 g, 7.5 mmol), and the mixture was stirred at room temperature. Intermediate 8 (2.6 g, 15.0 mmol) and sodium hydrogencarbonate (4.03 g, 48 mmol) were added thereto, and the mixture was stirred at 110C overnight. Water (70 ml) was added to thereaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: chloroform: methanol = 8: 2) to give the title compound (0.55 g, 29%).

The synthetic route of 369-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1227083; (2002); A1;,
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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. 107582-20-7 name is Methyl 2,3-diaminobenzoate, 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. 107582-20-7

Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35¡ãC.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10¡ãC. The solid was filtered, washed with 150 mlof water, and dried at 50-60¡ãC to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50¡ãC by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5¡ãC. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65¡ãC for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV).

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

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/15134; (2006); A1;,
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