Tag: M.W=100-200

Application of 5335-05-7,Some common heterocyclic compound, 5335-05-7, name is Chloromethyl benzoate, molecular formula is C8H7ClO2, 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.

The phosphinic acid (65mg, O.OSmmol) was suspended in 1.5mL of DMF.Chloromethyl benzoate (llSmg, O.Slmniol), triethylamine (167., 1.20mmol)and tetrabutyl ammonium iodide (TBAI) (7mg, 0.02mmol) were added. Thesolution was heated at 70C for 3 hours. The solution was cooled to roomtemperature, purified using a Reverse Phase Gilson HPLC to yield compound41 (20mg, 27%). :H NMR (300 MHz, CDsOD): 5 8.08 (dd, 2H), 7.63 (d, J=7.3Hz, 1H), 7.48 (d, J=6.4 Hz, 1H) 7.42 (s, 1H), 7.35 (s, 1H), 7.04 (d, J=9.1 Hz, 1H),5.98 (m, 1H), 5.95 (m, 1H), 5.60 (d, 2H), 5.44 (s, 1H), 5.33 (d, 1H), 5.18 (d, J=9.1Hz, 1H), 5.14 (d, J=9.1,1H), 4.87 (s, 1H), 4.5.2 (d, J=9.4,1H), 4.56 (d, 1H), 4.27 (s,1H), 3.94 (s, 3H), 2.66 (m, 1H), 2.58 (m, 1H), 2.37 (m, 1H), 2.14 (m, 1H), 1.64 (m,6H), 1.33 (d, 6H), 1.04 (s, 9H). 31P (75 MHz, CDsOD): 5 52.994, 57.542.

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

Reference:
Patent; GILEAD SCIENCES, INC.; WO2006/20276; (2006); A2;,
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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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., COA of Formula: C8H14O4

A 100 mL round-bottom flask equipped with a stirring bar was charged with compound 7 (1000 mg, 5.8 mmol) and DMF (20 mL). To the solution, sodium hydride (60percent oil suspension, 233 mg, 5.8 mmol) was added. The reaction was allowed to stir at 0 °C for 1 h. To the mixture, 4-bromobenzyl bromide (1437 mg, 5.8 mmol) was added at 0 °C and the mixture was stirred at room temperature for 20 h. To the reaction mixture, H2O was added, and the mixture was extracted with CH2Cl2 (3x), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexanes/AcOEt = 90:10) to afford the desired product 4 (1551 mg, 79percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.39 (d, J = 8.3 Hz, 2H), 7.08 (d, J = 8.3 Hz, 2H), 3.70 (s, 3H), 3.53 (t, J = 7.8 Hz, 1H), 3.13 (d, J = 7.8 Hz, 2H), 1.40 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 169.4, 167.5, 137.0, 131.5, 130.6, 120.5, 83.2, 54.3, 52.4, 34.0, 27.8; HR-FAB MS calcd for C15H20BrO4 [M+H]+ 343.0545, found 343.0558.

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:
Article; Kanemitsu, Takuya; Furukoshi, Saeka; Miyazaki, Michiko; Nagata, Kazuhiro; Itoh, Takashi; Tetrahedron Asymmetry; vol. 26; 4; (2015); p. 214 – 218;,
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5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, 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. SDS of cas: 5048-82-8

l-{[(benzyloxy)carbonyl]amino}cyclopentanecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq.) and triethylamine (3 eq.) were added, followed by ethyl (2u)-3-(4-aminophenyl)acrylate (0.95 eq.). The resulting mixture was stirred for 48 h at 40 0C. DMF was evaporated, the resulting oil taken up in EPO EtOAc and the solution washed with hydrochloric acid (3x, 1 M), water, a solution of saturated aqueous NaHCO3 (2x) and brine. Drying over sodium sulfate and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1, containing 1percent EtOH) as the eluant. The resulting solid was immediately dissolved in DCM (0.1 M) and triflic acid (5 eq.) was added dropwise at RT. After 5 min at RT, the red mixture was poured into an aqueous solution OfNaHCO3. The organic phase was separated, the aqueous phase was extracted with DCM (4x) and the combined organic phases dried over sodium sulfate. Evaporation gave the title compound as an off-white solid, which was used without further purification. 1H NMR (400 MHz, DMSO-fi?6, 300 K) delta 1.26 (t, J 7.1, 3H), 1.48-1.61 (m, 2H), 1.63-1.87 (m, 4H), 1.96-2.10 (m, 2H), 4.188 (q, J7.1 Hz, 2H), 6.53 (d, J 16.0, IH), 6.60-7.30 (bs, 3H), 7.59 (d, J 16.0, IH), 7.67 (d, J8.5, 2H), 7.76 (d, J8.5, 2H); MS (ES+) m/z 303 (M+H)+.

The synthetic route of 5048-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/29029; (2007); A2;,
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Reference of 13380-85-3, 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. 13380-85-3, name is Methyl 4-(hydroxymethyl)cyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

In a nitrogen atmosphere, 7.4 g of the compound represented by the formula (I-12), 4.1 g of pyridine and 35 mL of dichloromethane were put into a reactor. With cooling with ice, 5.4 g of methanesulfonyl chloride was dropwise added thereto, and stirred at room temperature for 3 hours. This was poured into water, and washed sequentially with 5% hydrochloric acid and salt water. Purification through column chromatography (silica gel, hexane/ethyl acetate) and recrystallization (acetone/hexane) gave 7.5 g of the compound represented by the formula (I-1-3).

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

Reference:
Patent; DIC Corporation; Horiguchi, Masahiro; Mamiya, Junichi; Aoki, Yoshio; (99 pag.)US2018/312481; (2018); 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. 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 294190-18-4

[0968] tert-Buty 4-{[5-chloro-3-(methoxycarbonyl)-2-methylphenyI]amino}piperidine-l- carboxylate[0969] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1.40 g, 7.04 mmol) in CH2CI2 (30 mL) and AcOH (2.50 g, 42.2 mmol) was added N-Boc piperidinone (1.96 g, 9.85 mmol) and sodium triacetoxyborohydride (4.40 g, 21 .1 mmol). The reaction mixture was stirred at 23 C for 1 8 hours and then saturated NaHC03 was added and the mixture was separated. The aqueous layer was extracted with CH2CI2 (3 x 20 mL) and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel columnchromatography (Si02 heptane/ethylacetate=10/l to 1 /1 ) to give the titled compound as oil (2.40 g, 89% yield). -NMR (400 MHz, CDC13) 5ppm; 7.09 (s, 1 H), 6.69 (s, 1 H), 4.05(m, 2H), 3.88 (s, 3H), 3.63 (m, 1 H), 3.42 (m, 1 H), 2.97 (m, 2H), 2.23 (s, 3H), 2.05 (m, 2H), 1 .45 (s, 9H), 1 .27 (m, 2H).

According to the analysis of related databases, 294190-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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Some common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. COA of Formula: C9H11NO2

4.6 g (28 mmol) of methyl 3-amino-6-methylbenzoate are dissolved in 50 ml of THF and 50 ml of 1M sulphuric acid and then the reaction medium is cooled to 0 C. A solution of sodium nitrite (2.3 g, 33.6 mmol) in 10 ml of water is then added dropwise and then the medium is stirred for 20 minutes. 15 ml of pure sulphuric acid are then added and the reaction medium is heated under reflux for 2 hours, poured into 500 ml of water and extracted with ethyl ether. The organic phases are dried, concentrated under reduced pressure and the residue obtained is dissolved in 100 ml of methanol. 3 ml of sulphuric acid are added and the reaction medium is heated under reflux for 14 hours, cooled, treated with water and ethyl ether. After extraction with ethyl ether, the organic phases are combined, dried over magnesium sulphate and concentrated under reduced pressure. After purification on a silica column (ethyl acetate 30-heptane 70), a brown oil is obtained (m=1.2 g; Y=25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18595-12-5, its application will become more common.

Reference:
Patent; Galderma Research & Development S.N.C.; US6689922; (2004); B1;,
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Reference of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

Step 1 : 4-(tert-Butyl-diphen l-silanyloxy)-cyclohexanecarboxylic acid ethyl esterTo a solution of ethyl 4-hydroxycyclohexane carboxylate (5.0 g, 29.03 mmol) in dichloromethane (200 mL) was added imidazole (4.97 g, 73 mmols) and tert- butylchlorodiphenylsilane (15.96 g, 15.2 mL, 58.0 mmol). The reaction mixture was allowed to stir at room temperature over night. The reaction mixture was poured into water (125 mL) in a separatory funnel and the phases were separated. The aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. Purification by column chromatography on silica gel eluting with ethyl acetate in heptanes (0-10%) afforded 10.55 g (89%) of the title compound.

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; GAO, Zhongli; HALL, Daniel; STEFANY, David; WO2011/143148; (2011); A1;,
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Reference of 1559-02-0, 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. 1559-02-0 name is Diethyl 1,1-cyclopropanedicarboxylate, 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: Diethyl cyclopropane-1,1-dicarboxylatederivatives (1.0 eq.) were dissolved in EtOH. KOH (1.0 eq.)in ethanol solution was added and stirred for 5 h. After the completion of the reaction, the intermediatewas dissolved in THF solution at 15 C. 4-Methylmorpholine (1.2 eq.), isobutyl chloroformate(1.0 eq.) and 4-amino-2-fluorophenol (1.0 eq.) were added. The crude product was purified by columnchromatography, and the above process was repeated. The final product compounds 12 were obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 1,1-cyclopropanedicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Yingnan; Zhang, Ke; Gao, Suyu; Wang, Guihua; Huang, Jian; Wang, Jinhui; Chen, Lixia; Molecules; vol. 21; 5; (2016);,
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Adding a certain compound to certain chemical reactions, such as: 33993-24-7, name is Cyclopropanecarboxylic anhydride, 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 33993-24-7, Computed Properties of C8H10O3

[0410] A solution of 315D (50.6 mg, 0.19 mmol) and cyclopropanecarboxylic acid anhydride (302 mg, 1.96 mmol) in dioxane (2 mL) was heated to 93 C. overnight. The mixture was concentrated in vacuo, diluted with EtOAc and washed with satd. Aq. KHCO3 solution (2×). The organic extract was dried (Na2SO4), filtered and concentrated. The residue was triturated with ether to obtain the title compound (11 mg, 17%) as a white solid.

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; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
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Related Products of 6914-71-2, The chemical industry reduces the impact on the environment during synthesis 6914-71-2, name is 1,1-Cyclopropanedicarboxylic acid dimethyl ester, I believe this compound will play a more active role in future production and life.

Reference Example 45 Production of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol To a solution of lithium aluminum hydride (9.34 g, 246 mmol) in THF (150 ml) was dropwise added a solution of dimethylcyclopropane-1,1-dicarboxylate (25.95 g, 164.1 mmol) in THF (150 ml) under ice cooling. The solution was stirred at 0 °C for 2 hours, and to the solution were slowly added water (9.5 ml), 15 percent aqueous solution of NaOH (9.5 ml) and water (30 ml), successively. Insoluble matters were filtered off, and the filtrate was concentrated to give cyclopropane-1,1-dimethylmethanol as colorless oily substance.

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, 1,1-Cyclopropanedicarboxylic acid dimethyl ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1591446; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics