Tag: M.W=100-200

Synthetic Route of 63485-50-7, 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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Triphenylphosphine-PS (3.27 g, 12.5 mmol) was added to a solution of 2- (difluoromethoxy)-5-fluorophenol (Intermediate 2D) (1 .85 g, 10.4 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3- hydroxycyclobutanecarboxylate (1 .33 mL, 12.5 mmol) was added, followed by DIAD (2.4 mL, 13 mmol). The reaction mixture was then warmed to room temperature, stirred for 12 h, filtered, and concentrated. The remaining material was purified on silica gel eluting with a 0%-70% EtOAc-hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (1 .79 g, 58%). 1H NMR (400 MHz, CD3SOCD3) delta 2.27-2.45 (m, 2 H), 2.57-2.79 (m, 2 H), 3.13-3.27 (m, 1 H), 3.32 (s, 3 H), 4.90 (dd, J = 7, 6 Hz, 1 H), 6.66-6.95 (m, 2 H), 7.03 (s, 1 H), 7.1 1 – 7.34 (m, 1 H); LC-MS (LC-ES) peak at T = 0.86 min.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Synthetic Route of 24812-90-6,Some common heterocyclic compound, 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, molecular formula is C9H11NO3, 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.

Anhydrous p-toluene sulfonic acid (25.0 g, 137.43 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (10 g, 55.25 mmol) obtained in step 1 of Preparation Example 1 and 2,4-difluorobenzonitrile (11.53 g, 82. 87 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (10.0 g, 31.22 mmol) in a yield of 57 %. 1H NMR (CDCl3): delta 8.31-8.22 (1H, m), 7.82-7.79 (1H, d), 7.65 (1H, s), 7.02-6.85 (3H, m), 3.88 (6H, s) MW: 320

The synthetic route of 24812-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); A1;,
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Electric Literature of 15963-40-3,Some common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, molecular formula is C7H10O2, 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.

a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 mm to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-1-carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 Cand methanol (20 mL) was added slowly and the mixture was stirred for 30 mm at 25 C. The reaction mixture was cooled to -10 C and H202 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 mm) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SO3 aqueous. The resulting solution was diluted with water (300 mL) andthen extracted with ethyl acetate (2×300 mL) and the organic layers combined. The resulting mixture was washed with brine (2×300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3 -(hydroxymethyl)cyclobutane- 1 -carboxylate as colorless oil (6.6 g, 58%).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 14064-10-9

To a stirring solution of M-2 (0.30 g) in acetone (30 ml) at ambient temperature is added diethyl chloromalonate (0.149 g) and K2CO3 (0.194 g). The resulting mixture is stirred for 16 h and solvent removed in vacuo. The residue is suspended between EtOAc/ H2O (100 ml each), the layers shaken, the organic layer separated, dried over Na2SO4, and solvent removed in vacuo. The residue is suspended in hexane, sonicated and filtered, to afford 0.295 g title compound as a white solid. 1H NMR (DMSO) delta0.83, 1.15, 1.50, 2.68, 2.95, 4.21, 4.92, 5.61, 6.83, 7.26, 7.49, 7.91; IR (mull) 3286, 1747, 1696, 1674, 1643, 1538, 1510, 1334, 1296, 1290, 1260, 1225, 1186, 1028, 698, cm-1. MS (FAB) m/z 586 (MH+), 586, 569, 434, 384, 305, 265, 176, 92, 91, 86. Anal. Found: C, 61.09; H, 6.56; N, 7.03.

According to the analysis of related databases, 14064-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia & Upjohn Company; US6353023; (2002); B1;,
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Electric Literature of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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 compound 1 (50 g, 276 mmol) in CHCb (600 mL) was added SO2CI2 (26 mL, 331 mmol) in an ice bath and stirred at reflux for 4 hours. The reaction mixture was concentrated to afford the crude product, which was purified by trituration with PE/EA = 1 : 1 (200 mL) to get desired product as white solid (36 g, 61% yield). 1H MR (400 MHz, DMSO-d6) delta: 7.64 (IH, s), 6.48 (IH, s), 3.81 (3H, s), 3.75 (3H, s).

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7ClO4S

7V-(3-Methyl-benzo[Z>]thiophen-2-yl)-2-carbomethoxy-ethanesulfonamide (600-A).; A solution of compound 757-A (1.0 g, 5.01 mmol) and pyridine (851 muL, 10.5 mmol) in dichloromethane (20 mL), cooled to 10 0C was treated with 3- chlorosulfonyl-propionic acid methyl ester (716 muL, 5.25 mmol) and stirred at ambient temperature for 18 h. The solvent was evaporated in vacuo, and the crude residue purified by flash column chromatography (SiO2), eluting with an ethyl acetate (10- 50%) in heptane gradient to afford 1.1 g of compound 600-A as an off white solid. 1H- NMR (DMSO-fe): delta 2.31 (s, 3H), 2.82 (t, 2H), 3.43 (t, 2H), 3.62 (s, 3H), 7.24-7.50 (m, 2H), 7.58-7.77 (m, IH), 7.80-7.95 (m, IH), 10.17 (s, IH); MS: m/z 314.1 (MH+).

The synthetic route of 15441-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2009/12430; (2009); A1;,
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Electric Literature of 924-99-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

ffl-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l-hvdroxy-3J-dimethylbutan-2- ylamino)acrylate.To a solution of 2,6-difluoro-5-iodonicotinic acid (4 g, 14.04 mmol, 1 equiv.) in toluene (30 mL) was added thionyl chloride (5.12 mL, 70.18 mmol, 5 equiv.) followed by DMF (0.5 mL). The reaction was stirred at 110 0C for 1 h. The reaction was concentrated. The residue was re-suspended in THF (15 mL) and added dropwise to a solution of ethyl-3- (dimethylamine)acrylate (2.1 mL, 14.04, 1,1 equiv.) and triethylamine (2.15 mL, 15.44 mmol, 1.1 equiv.) in THF (15 mL). The reaction was stirred at 67 0C for 2 h and cooled to 23 C. (5)-2-amino-3,3-dimethylbutan-l-ol (1.81 g, 15.44 mmol, 1.1 equiv.) was subsequently added and stirred at 23 0C for 30 min. The reaction was quenched with water (40 mL) and ethyl acetate (40 mL). The aqueous layer was extracted with ethyl acetate (2×40 mL), and the organics were dried and concentrated. The compound was purified via silica gel chromatography and concentrated to provide (5)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l- hydroxy-3,3-dimethylbutan-2-ylamino)acrylate Intermediate 80 (4.49 g, 66 %). Calcd for C17H21F2IN2O4 [M + H]+: 482.9.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIFULCO, Neil; CHOY, Allison, Laura; QUIROGA, Olga; SHERER, Brian; WO2010/136817; (2010); A1;,
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Application of 94994-25-9, A common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, molecular formula is C11H16O3, 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 stirred solution of methyltriphenylphosphonium bromide (9.1 g, 12.8 mmol) in THF (50 ml) at 0 C. was added potassium hexamethyldisilazide (0.5M in toluene, 48.6 ml), dropwise over 5 min. The resulting mixture was allowed to warm up to room temperature over 1 h, then cooled again to 0 C. and treated with methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate 15-A (Chapman, N. B. et al. J. Org. Chem., 1970, 35, 917) (2.5 g, 12.8 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with EtOAc (350 ml). The organic phase was washed with aqueous HCl (1 N), saturated aqueous sodium bicarbonate, and brine, then dried (Na2SO4) and concentrated in vacuo. The resulting solid was purified by flash silica gel chromatography, eluting with a gradient 0-4% EtOAc/hexanes. The resulting methyl 4-vinylbicyclo[2.2.2]octane-1-carboxylate 15-B was isolated as a clear, colorless oil.

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:
Patent; Waddell, Sherman T.; Santorelli, Gina M.; Maletic, Milana M.; Leeman, Aaron H.; Gu, Xin; Graham, Donald W.; Balkovec, James M.; Aster, Susan D.; US2004/133011; (2004); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 36692-49-6

Example 21: 3-Amino-6-{4-[2-hydroxy-2-(2-phenyl-lN-benzoimidazol-5-yl)- ethylamino]-piperidin-1-yl}-4-propyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide 0 0 o H i I so) Hunig’s base N -ire NH DCM 0 NH2 NH2 acetic acid H H THF / N N H min02 Mn02 N THE zon H 21 3,4-Diamino-benzoic acid methyl ester (2 g, 12.035 mmol) was dispersed in 40 mL DCM. Added hunig’s base (2.516 mL, 14.442 mmol) and stirred at RT until everything was in solution. Added benzoyl chloride (1.397 mL, 12.035 mmol) dropwise into the mixtuxe and stirred at RT for 1 hour. Added sat. NaHC03 aq. solution into the reaction mixture. Extracted with DCM three times. Combined all organic extracts and washed with brine. Dried over Na2SO4. Filtered and removed solvent in vacuo. Purified by flash chromatography using 10 % MeOH/DCM as eluent mixtures. 4-Amino-3-benzoylamino- benzoic acid methyl ester was trituated in hot ethyl acetate and 1.667 g (51.2 %) white solid was obtained.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/56562; (2005); A1;,
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Application of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

a) Ethyl 2-[2,5-difluorobenzoyl]-3-dimethylamino-2-propenoate; A solution of 2,5-difluorobenzoyl chloride (5.26 g) in toluene (100 mL) was treated with ethyl-3-dimethylamino-2-propenoate (5.27 g), followed by triethylamine (5.9 mL). The mixture was stirred at 90C for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated in vacuo to give a residue which was purified by flash chromatography (silica gel, 50-100% Et2O in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.2 [M+H]+, 306.1 [M+ Na]+.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
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