Tag: M.W=100-200

Electric Literature of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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 methyl 1-hydroxycyclopropanecarboxylate (0.741 mL, 8.61 mmol) was added diisopropylcarbamic chloride (1.550 g, 9.47 mmol) and DIEA (2.256 mL, 12.92 mmol) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was washed with 1 N HC1,water and brine, dried (Mg504), filtered and concentrated. The residue was purified via Biotage (15% to 30% EtOAc/Hex; 25 g column) to yield Cap L-9 Step a (0.66 g).

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

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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Synthetic Route of 18595-12-5, These common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 Preparation of 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea Methyl 5-amino-2-methylbenzoate (223 mg) was dissolved in tetrahydrofuran (30 ml), under ice-cooling triphosgene (135 mg) was added, triethylamine (116 mul) was added thereto five times every 3 minutes, the mixture was stirred for 10 minutes at same temperature. Subsequently, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in tetrahydrofuran (20 ml) was added dropwise, stirred for 30 minutes at same temperature, and then stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 271 mg of the titled compound. 1H-NMR(CDCl3) delta: 1.04(9H, s), 2.39(3H, s), 2.50(3H, s), 2.52(3H, s), 3.83(3H, s), 3.96(1H, dd), 4.34(1H, t), 4.43(1H, d), 4.79-4.89(1H, m), 5.50(1H, d), 6.01(1H, d), 6.89(1H, brs), 7.03(1H, s), 7.03-7.35(6H, m), 7.43(1H, t), 7.69(1H, d), 7.88(1H, d)

Statistics shows that Methyl 5-amino-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 18595-12-5.

Reference:
Patent; Zeria Pharmaceutical Co., Ltd.; US6239131; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, 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 344-14-9, Product Details of 344-14-9

Part A: 5-Fluoro-6-hydroxy-2,4(1H,3H)-pyrimidinedione. A mechanically stirred solution of urea (60.06 g, 1 mol) and dimethyl fluoromalonate (150.1 1 g, 1 mol) in methanol (1 L) was treated with 25 wt% NaOMe in methanol (-4.6M, 435 mL, 2 mol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The mixture was filtered, the wet cake was dissolved in warm water (-1.2L), and the resulting aqueous solution was acidified with concentrated aqueous HCI(-160 mL) to pH = 2 while stirring over 1 h. The mixture was allowed to cool to room temperature, and the product was filtered and washed thoroughly with water, then dried under vacuum to give 5-fluoro-6-hydroxy-2,4(1 H,3H)-pyrimidinedione (80 g, 55%) as a white solid. LCMS: (M+H)+: 147.0.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

First, put a stirrer in a 35 mL sealed tube, and then add 2-methyl-1-butene-3-yne (32 muL, 0.33 mmol), 0.9 mL tetrahydrofuran (0.9 mL), and 2-chloroacetamido Quinoline (66.2mg, 0.3mmol), dimethyl 2-fluoromalonate (70.4mg, 0.45mmol), to this mixed solution were added CuI (5.7mg, 0.03mmol) and Cs2CO3 (117.3mg, 0.36mmol), charge N2 for 3 minutes with a glass tube connected to nitrogen, fully drive out the air, seal the nozzle with a cock, and stir the reaction at 800C for 1.5 hours. After the reaction is completed, the system is cooled to room temperature and added to the reaction system. 2ml of distilled water was extracted with ethyl acetate. The organic phases were combined, and the solvent of the organic phase was distilled off under reduced pressure. 84.1 mg of product 4e was separated by silica gel column chromatography. The yield was 70%.

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

Reference:
Patent; Anyang Normal University; Lv Yunhe; Pu Weiya; Wang Xin; Wang Xiaoxing; (15 pag.)CN110627718; (2019); A;,
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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 94994-25-9 as follows. category: esters-buliding-blocks

Method B. 1 (9.81 g, 0.0500 mol) was dissolved in THF (100 mL). Diethyl cyanomethyl- phosphonate (8.90 mL, 0.0550 mol) was added. The mixture was cooled with an ice bath. Sodium tert-butoxide (5.28 g, 0.0550 mol) was added slowly. After 10 min, the suspension became a clear solution. After 2 h, aq NaOH (1M, 50 mL) was added. The mixture was stirred at room temperature overnight. To the reaction mixture was added water (100 mL) and MTBE (100 mL). The aqueous layer was separated and washed with MTBE (100 mL) cooled with ice batch and acidified with HCI (2M, 50 mL). The precipitate was collected by filtration and dried in a vacuum oven at 50 C overnight to yield the product (3) as white solid (7.92 g) in 72.2% yield.

According to the analysis of related databases, 94994-25-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC; KWOK, Daw-long, Albert; KIESMAN, William; HUMORA, Michael; CAI, Xiongwei; LITTKE, Adam; CHANG, HeXi; WO2011/63268; (2011); A2;,
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Reference of 90030-48-1, 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. 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of Intermediate 67 tert-butyl ((5-bromo-1H-pyrrolo[3,2-b]pyridin-2- yl)methyl)(methyl)carbamate (1.1912 g, 3.50 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (1.224 g, 7.03 mmol, Aldrich) and copper(I) iodide (1.34 g, 7.04 mmol) in Dimethyl Sulfoxide (DMSO) (18 ml) was degassed for 10 minutes under a flow of nitrogen. The reaction vessel was heated to 110 C and stirred at 110 C under nitrogen for 2h. Ethyl acetate (30 ml) was added to the reaction mixture, which was then filtered on Celite (lOg) and the residual solid washed with ethyl acetate (3×20 ml). The filtrate was washed with a mixture of water/aqueous saturated ammonium chloride / aqueous saturated sodium bicarbonate (4: 1: 1 60 ml), and water (60 ml). The aqueous layer was further extracted with ethyl acetate (50 ml) and the organic phases combined. The organic phase was further washed with a mixture of water/aqueous saturated ammonium chloride / aqueous saturated sodium bicarbonate (4: 1: 1 60 ml), and water (60 ml), followed by brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to yield methyl 3-((2- (((tertbutoxycarbonyl)(methyl)amino)methyl)-1H-pyrrolo[3,2-b]pyridin-5-l)sulfonyl)- propanoate (1380 mg, 3.35 mmol, 96% yield). LCMS (System B, UV, ESI): Rt = 0.92 min, [M+H]+ 412

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, Sodium 3-methoxy-3-oxopropane-1-sulfinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BRAVI, Gianpaolo; HOBBS, Heather; INGLIS, Graham George Adam; NICOLLE, Simon; PEACE, Simon; (138 pag.)WO2019/115640; (2019); A1;,
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Electric Literature of 14062-18-1, 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. 14062-18-1 name is Ethyl 2-(4-methoxyphenyl)acetate, 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.

General procedure: To the stirred solution propargyl alpha-(4-methoxyphenyl)acetate 6a (2.04 g, 10 mmol) in 15 mL acetonitrile was added 4-acetamidobenzenesulfonyl azide (2.88 g, 12 mmol) and DBU (2.24 mL, 15 mmol) at ambient temperature under inert atmosphere. The reaction mixture was stirred for 16 h at room temperature. The reaction was quenched with saturated NH4Cl and the product was extracted with diethyl ether (30 mL x 3). The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The extract was filtered and the filtrate was evaporated under vacuum. The crude product was purified using column chromatography over silica gel to afford propargyl alpha-(4-methoxyphenyl)-alpha-diazoacetate 1a as orange solid (1.934 g, 84% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(4-methoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Article; Navale, Balu S.; Laha, Debasish; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 60; 29; (2019); p. 1899 – 1903;,
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Electric Literature of 87661-20-9, The chemical industry reduces the impact on the environment during synthesis 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

tert-Butyl 1-allylcyclopropanecarboxylate STR11 A solution of 34.1 g (0.24 mol) of tert-butyl cyclopropanecarboxylate in 25 ml of tetrahydrofuran was added dropwise at -70 C. to a mixture of 33.6 ml (0.24 mol) of diisopropylamine, 150 ml of a 1.5 molar solution of n-butyllithium in n-hexane (=0.24 mol of butyllithium) and 100 ml of tetrahydrofuran. Stirring was carried out for 3 hours at -70 C., after which a solution of 27.8 g (0.23 mol) of allyl bromide in 25 ml of tetrahydrofuran was added dropwise. Thereafter, the reaction mixture was stirred for a further 2 hours at -70 C. and then for 12 hours at 20 C. After hydrolysis with 50 ml of saturated aqueous ammonium chloride solution and after phase separation, the organic phase was worked up in a conventional manner to obtain the product. The crude product was purified by distillation. Yield: 61%, bp.: 86-88 C. at 30 mbar; colorless oil.

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, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US5371268; (1994); A;,
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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. 103-25-3, name is Methyl 3-phenylpropionate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H12O2

Several other esters, whose structure and names are described in Table 3, were hydro genated under the conditions described above using preformed RuCl2(L-I). Isolated yield are given in Table 4.Table 3: Structure and names of substrates usedTable 4: Hydrogenation of esters using RuCl2(L-I) EPO Sub.: Substrate as described in Table 3.Conv.: Conversion (in %, analysed by GC after silylation) of ester to alcohol after 2h30min.Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I) 0.05 mol%,NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 103-25-3.

Reference:
Patent; FIRMENICH SA; WO2006/106484; (2006); A1;,
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Reference of 4630-80-2, 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. 4630-80-2 name is Methyl cyclopentanecarboxylate, 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.

n-Butyllithium (2.5 M in hexanes) (1.24 ml, 3.09 mmol) was addeddropwise to a -78 oc solution of diisopropylamine (0.440 ml, 3.09 mmol) in tetrahydrofuran(THF) (13 ml). The mixture was allowed to warm to room temperature and stirred for 15minutes. The mixture was cooled to -78 oc before methyl cyclopentanecarboxylate (0.355ml, 2.81 mmol) was added dropwise. The mixture was warmed to 0 oc and stirred for 30minutes before being cooled again to -78 C. A solution of 2-(benzyloxy)-4-(bromomethyl)-1-methoxybenzene (1.035 g, 3.37 mmol) in tetrahydrofuran (THF) (5 ml) was addeddropwise. The mixture was stirred an additional 15 minutes at -78 oc and then allowed towarm to room temperature and stirred overnight. The mixture was diluted with ethylacetate, washed with saturated ammonium chloride, washed with brine, and concentrated.The residue was purified by medium pressure reverse phase chromatography (C18 Iacetonitrile I water I 0.1% formic acid I 10% to 100% gradient). Fractions wereconcentrated. The residue was dissolved in acetonitrile and the mixture concentrated in order to azeotrope remaining water. Drying under vacuum gave methyl 1-(3-(benzyloxy)-4-methoxybenzyl)cyclopentane-1-carboxylate (716 mg, 2.02 mmol, 72 % yield) as a clear oil.LCMS (ESI) mlz: 377.3 (M+Nat.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
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