Month: November 2020

Adding some certain compound to certain chemical reactions, such as: 2876-78-0, name is Methyl 1-Naphthaleneacetate, 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 2876-78-0. 2876-78-0

alpha-(N-tert-Butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester alpha-(1-Naphthyl)-acetic acid methyl ester (150 mg, 0.75 mmol) was dissolved in tetrahydrofuran. To the solution, hexamethylphosphoramide (HMPA, 671 mg, 3.75 mmol) was added, and the mixture was cooled to -78 C. To this solution, lithium diisopropylamide (1.5 M solution in cyclohexane, 0.75 ml, 1 mmol) was added dropwise, and the mixture was stirred at -78 C. for 30 minutes. Then, a tetrahydrofuran solution (2 mL) of N-tert-butoxycarbonyl-6-amino-1-iodohexane (270 mg, 0.82 mmol) was added dropwise thereto, and the mixture was stirred at -78 C. for 1 hour. The temperature of the reaction solution was raised to 0 C. over 15 minutes, and then, water (50 mL) was added to the solution, followed by extraction with ethyl acetate (50 mL) twice. The organic layer was washed with a saturated ammonium chloride solution (20 mL) and subsequently brine (20 mL) and then dried over sodium sulfate to dryness under reduced pressure. The reaction product was purified by silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain alpha-(N-tert-butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester (271 mg, yield: 91%): 1H NMR (400 MHz, CDCl3): delta 8.11 (d, J=8.5 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.40-7.54 (m, 4H), 4.71 (s, 1H), 4.36 (t, J=7.8 Hz, 1H), 3.61 (s, 3H), 3.04 (m, 2H), 2.07 (m, 2H), 1.24-1.48 (m, 17H); 13C NMR (100 MHz, CDCl3): delta 174.7, 155.9, 135.3, 133.8, 131.3, 128.8, 127.5, 126.1, 125.4, 125.3, 124.6, 122.8, 78.7, 51.8, 46.5, 40.3, 32.9, 29.7, 28.9, 28.2, 27.6, 26.3; FAB-MS: m/z [M+H]+ 400.

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 Methyl 1-Naphthaleneacetate.

Reference:
Patent; TOHOKU UNIVERSITY; KAKE EDUCATIONAL INSTITUTION; KANAGAWA PREFECTURAL HOSPITAL ORGANIZATION KANAGAWA CHILRDEN’S MEDICAL CENTER; ABE, Takaaki; TOMINAGA, Teiji; HAYASHI, Kenichiro; OSAKA, Hitoshi; US2015/353489; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, molecular formula is C4H7NaO4S, 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. 90030-48-1.

Methyl 3 -( 1 -((2-(trimemylsilyl)ethoxy)methyl)- 1 H-pyrrolo [2,3 -b]pyridin-5- ylsulfonvDpropanoate (4-lb) To a nitrogen gas purged sealable vial of 5-bromo-l-((2-( methylsilyl)ethoxy)methyl)-lH-pyrrolo[2,3-b]pyridine 4-la (3000 mg, 9.17 mmol), copper(i) iodide (6983 mg, 36.7 mmol) and sodium 3-methoxy-3-oxopropane-l-sulfinate(TYGER) (6385 mg, 36.7 mmol) was added DMSO (15 ml) . The reaction mixture was heated in an oil bath at 105c for 18hrs. LCMS analysis showed reaction to be a mixture of desired ester and acid. The reaction was quenched into ethyl acetate (200 ml) and water (200 ml) and the ph adjusted from 7 to 3 with IN HC1. The reaction was filtered thru celite and sand and the filtrate layers separated. The organic which contained a mix of acid and ester was dried over sodium sulfate, filtered and concentrated to an oil. The oil was azeotroped with toluene to remove any remaining water to give a brown oil, 3.4 gms. The oil was dissolved in dichloromethane (20 ml) and methanol (20.00 ml) cooled to 0C and TMS-Diazomethane (4.94 ml, 9.88 mmol) slowly added dropwise. The reaction was stirred at 0C for 10 minutes, quenched with aq. KHSO4 and allowed to stir at room temperature for 1 hr. The reaction was concentrated to remove methanol and the product extracted into ethyl acetate (100 ml), dried over sodium sulfate and concentrated to oil . The oil was chromatographed on silica (100 g, 0-50% ethyl acetate/hexanes) to give the product 4-lb as oil, 1.46 g . LRMS (ESI) m/z 399.1 [(M+H)+; calcd for C17H26N205SSi: 399.1 ].

The synthetic route of Sodium 3-methoxy-3-oxopropane-1-sulfinate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUTCHER, John, W.; WITTER, David; DINSMORE, Christopher; KIM, June; HENDRIX, John; ARCHARYA, Raksha; AHEARN, Sean, P.; JUNG, Joon; RIVKIN, Alexey; JONES, Philip; WO2013/52355; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, I believe this compound will play a more active role in future production and life. 14062-25-0

Step a: Diethyl 2-(4-bromophenyl)malonate To a solution of ethyl 2-(4-bromophenyl)acetate (5.0 g, 21 mmol) in dry THF (40 mL) at -78 C. was added a 2.0M solution of lithium diisopropylamide in THF (11 mL, 22 mmol). After stirring for 30 minutes at -78 C., ethyl cyanoformate (2.0 mL, 21 mmol) was added and the mixture was allowed to warm to room temperature. After stirring for 48 h at room temperature, the mixture was quenched with water (10 mL). The reaction was partitioned between 1 N HCl (50 mL) and dichloromethane (50 mL), and the organic layer was separated. The organic layer was washed with 1 N HCl (50 mL), dried over Na2SO4 and evaporated. The crude material was purified by silica gel chromatography, eluding with 0-20% ethyl acetate in hexanes to give diethyl 2-(4-bromophenyl)malonate (2.6 g, 41%) 1H NMR (400 MHz, DMSO-d6) delta 7.60-7.58 (m, 2H), 7.36-7.34 (m, 2H), 5.03 (s, 1H), 4.21-4.09 (m, 4H), 1.20-1.16 (m, 6H).

The chemical industry reduces the impact on the environment during synthesis 14062-25-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hadida Ruah, Sara S.; Miller, Mark T.; Bear, Brian; McCartney, Jason; Grootenhuis, Peter D. J.; US2008/9524; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4897-84-1,Some common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, molecular formula is C5H9BrO2, 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.

Compound 125:[250] To a solution of IBD monomer 8 (118 mg, 0.4 mmol) and methyl 4-bromobutyrate (109 mg, 0.6 mmol) in anhydrous DMF (1.5 mL) was added potassium carbonate (111 mg, 0.8 mmol). The mixture was stirred at room temperature overnight and diluted with ethyl acetate, washed with saturated ammonium chloride and brine. It was dried over anhydrous sodium sulfate and filtered. The filtrate was striped under reduced pressure to give compound 125 (146 mg, y = 93percent) as a yel]ow foam. 1R NMR (400 MHz, CDCl3): delta 8.25 (d, J = 8.0 MHz, IH), 7.84 (d, J = 4.4 MHz, IH), 7.52 (s, IH), 7.26-7.22 (m, 2H), 7.10-7.06 (m, IH), 6.81 (s, IH), 4.44 (dt, J1 = 10.8 MHz, J2 = 4.0 MHz, IH), 4.15-4.07 (m, 2H), 3.92 (s, 3H), 3.68 (s, 3H), 3.67-3.64 (m, IH), 3.46- 3.43 (m, IH), 2.55 (t, J = 7.2 MHz, 2H), 2.22-2.15 (m, 2H); MS (ESI, m/z): found 465.2 (M + MeOH + K) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromobutanoate, its application will become more common.

Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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. 37466-90-3

Step 6-1-1 Ethyl 2,3-dimethylquinoxaline-6-carboxylate Ethyl 3,4-diaminobenzoate (500 mg, 2.77 mmol) and diacetyl (238 mg, 2.77 mmol) were dissolved in ethanol (20 ml), and the mixture was heated under reflux. One hour after, diacetyl (30 mg) was added thereto, and the mixture was heated under reflux. After the mixture was heated under reflux for 2.5 hours in total, the reaction solution was poured into water, and the precipitate was separated by filtration and washed with water. By through circulation drying for 15 hours, the title compound (650 mg, quantitative) as a light-brown powder was obtained. 1H-NMR (DMSO-d6) delta: 8.52 (d, J=1.5 Hz, 1H), 8.19 (dd, J=1.9, 8.5 Hz, 1H), 8.07 (d, J=8.5 Hz, 1H), 4.40 (q, J=6.9 Hz, 2H), 2.72 (s, 3H), 2.72 (s, 3H) Mass, m/z: 230 (M+), 185 (base)

Statistics shows that 37466-90-3 is playing an increasingly important role. we look forward to future research findings about Ethyl 3,4-diaminobenzoate.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2905-54-6, name is Methyl 2,3-dichlorobenzoate, A new synthetic method of this compound is introduced below., 2905-54-6

A suspension of 10.56 g of lithium aluminium hydride in 125 ml of THF is cooled to 0 C., a solution of 25.68 g of the compound obtained in the preceding step in 100 ml of THF is added dropwise, the temperature is allowed to return to RT and the mixture is kept stirred for 2 hours at RT. The reaction mixture is diluted by adding 250 ml of THF and hydrolysed by adding 11 ml of water, 11 ml of 4N NaOH and 33 ml of water. It is allowed to stand overnight at RT, the inorganic salts are filtered and the filtrate is concentrated under vacuum. 21.54 g of the expected product are obtained after drying under vacuum at 30 C.

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; Emonds-Alt, Xavier; Proietto, Vincenzo; US2004/180890; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

61367-07-5, 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 61367-07-5 as follows.

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (93.0 g) obtained in Reference Example 2(1) is dissolved in methanol (1000 ml), and thereto are added 35 % aqueous formaldehyde solution (95.4 ml), sodium acetate (39.4 g) and 10 % palladium/carbon (10 g). The mixture is then stirred at room temperature for 3.5 hours under atmospheric hydrogen pressure. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. To the resulting residue is poured 20 % aqueous potassium carbonate solution (500 ml), and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate and potassium carbonate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 2/1) to give methyl trans-4-dimethylaminocyclohexanecarboxylate (87.3 g). APCI-MS M/Z:186[M+H]+.;

According to the analysis of related databases, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

538-23-8, The chemical industry reduces the impact on the environment during synthesis 538-23-8, name is Propane-1,2,3-triyl trioctanoate, I believe this compound will play a more active role in future production and life.

Two mg of a free astaxanthin (manufactured by Sigma) and 300 mg of tricaprilin as a triglyceride form fatty acid were placed in a brown glass bottle. Three hundred mg of the immobilized lipase, Novozym435 (manufactured by Novozymes, Japan Ltd.), obtained by immobilizing lipase derived from Candida was added thereto, and 30 muL of water was further added thereto and stirred fully afterwards. Thereafter, while stirring, reaction was carried out at 45C. Three days later, the reaction solution was taken out, and the composition ratio of astaxanthin was analyzed by HPLC. As a result, the composition ratio was 99.0% astaxanthin, 1.0% monoester, and less than 1% diester.

The chemical industry reduces the impact on the environment during synthesis Propane-1,2,3-triyl trioctanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNTORY LIMITED; EP1500645; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

106614-28-2, 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 106614-28-2 as follows.

To a 50 mL round bottom flask purged with and maintained 1..mder an inertatmosphere of nitrogen v.¡¤as added (1 S,4S,5R)-5-[[5-cyclopropyl-3-(2,6-dichloropheny l)- L2-oxazol-4-yl]rnethoxy]-2-azabicyclo[2.2.1]heptane hydroiodide salt l2dd (250 rng, 0.49 mmol, 1.00 equiv.), methyl2,4-dit1uorobenzoate (225 mg, 1.31 mmol, 2.67 equiv.), CsF (298rng, 196 mmol, 4.00 equiv.), and 1-Ethyl-3-methylimidazoliurn dimethyl phosphate (3 mL)The resulting mixture was heated at 90C overnight After cooling to room temperature, themixtme wa;;; diluted with 20 mL off-hO and extracted with ethyl acetate (30 mL x 2). The5 cornbined organic extracts were washed with brine (30 mL x 3), dried over anhydrous sodiumsulfate and concentrated under vacuum. The residue was purified by silica gel columnchromatography eluting ~ith ethyl acetate/petroleum ether (I: 3). Removal of solventsafforded methy 14-[(1 S,4S,5R)-5-[[5-cydopropyl-3-(2,6-dichloropheny 1)-1,2-oxazol-4-y l]methoxy]-2-azabicyclo[2.2.l ]hepi:m-2-yl]-2-fluorobenzoate T-177 (158 6 mg, 50%) as an10 off-white solid. 1H-NMR (300 MHz, CDCb): 8 7.77 (t, J = 8.7 Hz, lH), 7.49-7.29 (m 3H),6.22 (dd, J ” 8.8, 2.4 Hz, 1H), 6.10 (dd, J ” 14.3, 2.3 Hz, 1H), 4.28 (s, 2H), 4.04 (s, lH), 3.87(s, 3H), 3.54- 3.44 (m, H-T), 3.35 (dd, J ‘” 9.3, 4.0 Hz, 1H), 2.63- 2.49 (m, 2H), 2.12 (ddt, J= 12.9, 9.6, 4.8 Hz, lH), l 85 (ddd, J = 13.3, 6.8, 2.4 Hz, IH), 1.71 – 1..54 (m, 2H), 1.41-1.22 (m, 3H), 1.27–1.03 (m, 2H): MS (ES, mlz): [M+1] = 531.05.

According to the analysis of related databases, Methyl 2,4-difluorobenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

15964-79-1, Adding a certain compound to certain chemical reactions, such as: 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)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 15964-79-1.

General procedure: To a mixture corresponding ester (9a-n, 5.0 mmol) and hydrazine monohydrate (15.0 mmol) in ethanol, catalytic amount of pyridine (0.5 mL) was added and refluxed for 10 h. The reaction was monitored by TLC. After the completion of the reaction, ethanol was evaporated from the mixture, water was added and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum to get the crude mass. Finally, the products 10a-n were purified using column chromatography. (Yield 80-85%).

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-(3,4-dimethoxyphenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Manickam, Manoj; Boggu, Pulla Reddy; Pillaiyar, Thanigaimalai; Sharma, Niti; Jalani, Hitesh B.; Venkateswararao, Eeda; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2369 – 2374;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics