Month: September 2021

Some common heterocyclic compound, 14062-19-2, name is Ethyl p-Tolylacetate, molecular formula is C11H14O2, 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: C11H14O2

LiHMDS was prepared by the treatment of HMDS (2.432 g, 15.07 mmol) with n-BuLi (1.6 M solution in hexane, 9.4 mL, 15 mmol) in dry THF (30 mL) at 0C for 30 min. To a solution of ethyl p-tolylacetate (1.778 g, 9.98 mmol) in dry THF (30 ml) was added the LiHMDS at -78C. The mixture was stirred at -78C for 30 min. To the mixture, ethyl cyanoformate (1.110 g, 11.20 mmol) was added at -78C, and then the mixture was allowed to warm to 0C for 80 min. 10% HCl was added at 0C, and the mixture was extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4. After removal of the solvent, the residue was purified by column chromatography using silica gel (hexane/acetone 25/1) to afford 7 as a colorless oil (2.396 g, 96%). 1H NMR spectra data were identical to those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-19-2, its application will become more common.

Reference:
Article; Kawasaki, Masashi; Kuroyanagi, Saki; Ito, Takuya; Morita, Hiroyuki; Tanaka, Yasuo; Toyooka, Naoki; Tetrahedron; vol. 73; 15; (2017); p. 2089 – 2099;,
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Electric Literature of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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.

General procedure: To a solution of compounds 1a-1e or methyl 4-aminobenzoate (1.0 mmol) in pyridine (3.0 mL), the corresponding sulfonyl chloride (1.3 mmol) in pyridine (3.0 mL)were added dropwise under nitrogen atmosphere at 0 C, then the reaction mixture was stirred at room temperature overnight. The reaction was then acidified to pH=1 with 4NHCl(aq) and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography (ethyl acetate-petroleum ether = 1:2) to give the title compounds 2a-2i.

Statistics shows that Methyl 4-chlorosulfonylbenzoate is playing an increasingly important role. we look forward to future research findings about 69812-51-7.

Reference:
Article; Zhang, Jiankang; Shen, Luqing; Wang, Jincheng; Luo, Peihua; Hu, Yongzhou; Medicinal Chemistry; vol. 10; 1; (2014); p. 38 – 45;,
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Application of 56441-97-5, A common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, 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.

Commercially available methyl 4-hydroxy-3-methoxy-benzoate 1 was converted in 5 steps to 4-(3-fluoroanilino)-6-methoxy-7-benzyloxy-quinazolme 15 (35% overall yield).[17,18] The only significant modification involved an improved workup of the nickel chloride hexahydrate-sodium borohydride reduction of the nitro intermediate. Debenzylation with trifluoroacetic acid to give the 7-hydroxy intermediate 16, followed by alkylation with propargyl bromide in acetonitrile, gave 13 in a 65% yield for 2 steps. This method involved an additional step, and the overall yield was greater. In addition, the final 7-hydroxy intermediate 16 could be used to generate other products [19].

The synthetic route of 56441-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; HANSON, Robert, N.; WO2010/85747; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 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 581065-95-4, name: tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

To a solution of Compound 6a (66 mg, 0.2 m mole) in dichloromethane (1 mL) were added DCC (47 mg, 0.22 m mole), HOBt (31 mg, 0.22 mmole) and the compound 4 (50 mg, 0.2 m mole). The mixture thus obtained was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by flash chromatography on silica gel with 1 % methanol in dichloromethane as eluent to give the title compound as an yellow oil (70 mg, 62%). ¹H NMR 8 1.44 (s, 9H), 2.51 (t, 1H), 2.63 (t, 2H), 2.93 (d, 3H), 3.01 (t, 2H), 3.45 (m, 2H), 3.55 (m, 2H), 3.64 (m, 12H), 3.71 (t, 2H), 5.01 (bs, 1H), 6.38 (bt, 1H), 6.62 (m, 2H), 7.27 (m, 1H), 7.43 (dd, 1H). MS (ES) 491 (M-56+H+), 513 (M- 56+Na+), 547 (M+H+), 569 (M+Na+) Compound 11b: ¹H NMR 8 1.34 (d, 3H), 1.45 (s, 9H), 2.30 (m, 1H), 2.5 (t, 2H), 2.69 (m, 1H), 2.93 (d, 3H), 3.37-3.55 (m, 5H), 3.63 (m, 12H), 3.71 (t, 2H), 4.99 (bs, 1H), 6.13 (bt, 1H), 6.62 (m, 2H), 7.25 (m, 1H), 7.48 (dd, 1H). MS (ES) 505 (M-56+H+), 527 (M-56+Na+), 543 (M-56+K+), 561 (M+H(at), 583 (M+Na(at). Compound lie: 1.43 (s, 3H), 1.45 (s, 9H), 2.46 (s, 2H), 2.5 (t, 2H), 2.92 and 2.94 (2s, 3H), 3.33 (m, 2H), 3.47 (t, 2H), 3.63 (m, 12H), 3.70 (t, 2H), 6.06 (bt, 1H), 6.63 (m, 2H), 7.25 (m, 1H), 7.54 (d, 1H); MS (ES) 519 (M-56+H(at), 541 (M-56+Na+), 575 (M+H(at), 597 (M+Na+).

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 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDAREX, INC.; WO2005/112919; (2005); A2;,
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Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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. Recommanded Product: 935273-86-2

Benzyl 3,3-difluorocyclobutanecarboxylate (2-C) (0.84 g, 3.72 mmol) was dissolved in ethanol (40 ml), and approximately 20 mg of palladium on activated carbon was added. The mixture was stirred at room temperature under hydrogen atmosphere for 12 hours, and then filtered through a pad of Celite. The filtrates were concentrated and dried in vacuo to give 2-D. lH NMR (500 MHz, CDCI3): delta2.86-2.93 (4H, m), 3.02-3.04 (IH, m) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935273-86-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/47625; (2007); 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. 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Formula: C9H8F3NO2

To a mixture of methyl 3-amino-4-(trifluoromethyl)benzoate (15 g, 0.073 mol) and aqueous HC1 solution (i2 M, 24 mL) in H20 (i00 mL) at 0 C was added dropwise a solution of NaNO2 (5.5 g, 0.080 mol) in H20 (30 mL). The reaction was stined at 0 C for 30 mm and then added dropwise to a sluny of CuCN (7.1 g, 0.080 mol) and KCN (8.4 g, 0.i3 mol) in H20 (200 mL), while maintaining the internal temperature between 5-1 0 C. After the addition was complete, the reaction was heated at 80 C for 1 h. The mixture was cooled and the solution was extracted with EtOAc (200 mL x 4). The combined organic layers were dried over anhydrous Na2504 and concentrated. The residue was purified by column chromatography on silica gel (2% EtOAc in PE) to afford the title compound. MS: m/z = 230.0 (M + 1). ?H NMR (400 MHz, CDC13)oe 8.46-8.53 (m, 1H), 8.33-8.42 (m, 1H), 7.87-7.95 (m, 1H), 4.01 (s, 3H).

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; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
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Reference of 1215205-50-7, 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 1215205-50-7 as follows.

Step 4: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3 g, 13.mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2. The solution was purged with N2 for 10 minutes, then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

According to the analysis of related databases, 1215205-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amira Phamaceuticals, Inc.; US2011/82181; (2011); A1;,
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Electric Literature of 99548-54-6,Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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 110 methyl { (3S) -6- [ (3-bromo-2-methylbenzyl) amino] -2, 3-dihydro-l- benzofuran-3-yl } acetate; [0990][0991]Methyl 3-bromo-2-methylbenzoate (2.29 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL) , under ice-cooling, lithium aluminum hydride (0.285 g, 7.50 mmol) was added by small portions, and the mixture was stirred under a nitrogen atmosphere for 2 hr. Sodium sulfate 10 hydrate (2.42 g, 7.50 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized from heptane-ethyl acetate to give 3-bromo-2-methylbenzyl alcohol (1.76 g, yield 88%) as colorless crystals. This product (0.943 g, 4.69 mmol) was dissolved in acetonitrile (25 mL) , a Dess-Martin reagent (2.39 g, 5.63 mmol) was added by small portions under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A solution of the obtained colorless oil, methyl [ (3S) -6-amino-2, 3-dihydro-l- benzofuran-3-yl] acetate (0.972 g, 4.69 mmol) and acetic acid(0.537 mL, 9.38 mmol) in acetonitrile (25 mL) was stirred under a nitrogen atmosphere at room temperature for 0.5 hr. Sodium triacetoxyborohydride (1.99 g, 9.38 mmol) was added to the reaction mixture, and the mixture was further stirred for 12 hr. The reaction mixture was treated with water and saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate rhexane = 5:95-40:60) to give the title compound (1.59 g, yield 87%, 2 steps) as a colorless oil.1H NMR (300 MHz, CDCl3) delta 2.42 (3H, s) , 2.48-2.59 (IH, m) , 2.68-2.78 (IH, m) , 3.68-3.83 (4H, m) , 3.89 (IH, br s) , 4.18- 4.30 (3H, m) , 4.71 (IH, t, J = 9.1 Hz), 6.07-6.16 (2H, m) , 6.93 (IH, d, J = 8.0 Hz), 7.01 (IH, t, J = 7.9 Hz), 7.23-7.30(IH, m) , 7.49 (IH, dd, J = 7.9, 1.1 Hz). MS m/z 390 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; NEGORO, Nobuyuki; TERAO, Yoshito; MIKAMI, Satoshi; YUKAWA, Tomoya; WO2010/143733; (2010); A1;,
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Electric Literature of 154825-97-5, 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of 2-(4-Bromophenyl)-2-methylpropanoic acid; [0525] A solution of methyl 2-(4-bromophenyl)-2,2-dimethylacetate(3880 muL, 15090 mumol) in EtOH (80 mL) and water (20 mL) was treated with KOH (4233 mg, 75450 mumol). The reaction was heated to 900C. After 15 hours, the reaction was cooled to 23C and concentrated in vacuo. The crude mixture was partitioned between water/diethyl ether (150 mL each). The aqueous layer was separated and extracted with diethyl ether (100 mL). The combined ether layers were then extracted with a IN NaOH solution (25 mL). The combined aqueous washes were acidified with concentrated HCl to pH = 2.0 and extracted with EtOAc (3 x 100 mL). The combined EtOAc layers were dried over MgSO4, and concentrated in vacuo to afford 3144 mg of 2-(4- bromophenyl)-2-methylpropanoic acid.

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 2-(4-bromophenyl)-2,2-dimethylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 32122-09-1, name is Ethyl 2-(benzyloxy)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 32122-09-1, Safety of Ethyl 2-(benzyloxy)acetate

To a solution of ethyl 2-(benzyloxy)acetate (1.30 g, 6.69 mmol) in anhydrous THF (30 mL) at -78 C was added dropwise LDA (2.0 M, 4.40 mL). The mixture was stirred for 30 min, and then tert-butyl 4-oxopiperidine-l-carboxylate (1.15 g, 5.77 mmol) in anhydrous THF (20 mL) was added. The mixture was stirred at -78 C for 1 hour, then quenched with sat aqueous H4CI (30 mL) and extracted with EtOAc (50 mLx3). The combined organic extracts were washed with brine and dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column (25% EtOAc in pet ether) to give the desired product as a colorless oil (1.82 g). Yield 80% (95% purity, UV=214 nm, ESI 294.1 (M+H)+).

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

Reference:
Patent; LAZULI, INC.; HARRISON, Bryce, Alden; BURSAVICH, Matthew, Gregory; GERASYUTO, Aleksey, Lgorevich; HAHN, Kristopher, Neil; KONZE, Kyle, David; LIN, Fu-Yang; LIPPA, Blaise, Scott; LUGOVSKOY, Alexey, Alexandrovich; ROGERS, Bruce, Nelsen; SVENSSON, Mats, Ake; TROAST, Dawn, Marie; (0 pag.)WO2018/160522; (2018); A1;,
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