Category: esters-buliding-blocks

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. 25542-62-5, name is Ethyl 6-bromohexanoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H15BrO2

Example 9.1 (0321) (0322) Ethyl 2-methyl acetoacetate (29.2 mL, 0.203 mol. 1 eq), 21% sodium ethoride solution (64 mL, 0.816 mol, 4 eq), ethyl 6-bromohexanoate (34 mL, 0.192 mol, 1 eq) and ethanol (200 mL) are added and the mixture is subjected to reflux at 120 C. for 12 hours. Next, the solvent is neutralized with 1M hydrochloric acid and extraction is carried out by using chloroform and distilled water. The extracted solvent is dried under reduced pressure and purification is carried out by normal phase chromatography to obtain the target compound (36.8 g, 63.4%). (0323) Rf=0.34 (Silica gel, hexane/ethyl acetate=10:1 v/v)

According to the analysis of related databases, 25542-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BioActs Co., Ltd.; PARK, Jin Woo; JANG, Su-Jung; KIM, Kiwon; SHIN, Gyeong Rim; LEE, Bongkyu; (52 pag.)US2017/313883; (2017); A1;,
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Synthetic Route of 581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, This compound has unique chemical properties. The synthetic route is as follows.

Example 9: Preparation of Compounds 10a and 10b [00172] Compound 8 (1.0 g, 1.97 mmol) was dissolved in DMF (25 mL) and Et3N (1.37 mL, 9.87 mmol) and cooled to 0 C. Then TSTU (593 mg, 1.97 mmol) was added and the reaction was stirred at 0 C for 30 minutes. A solution of the appropriate pegylated amine (2.07 mmol) in chloroform (10 mL) was added dropwise at 0 C and the reaction was allowed to warm to room temperature and stir for 12 hours. The reaction was concentrated and the -Bu ester of lOa/lOb was purified by silica gel chromatography (acetonitrile/methanol). The purified -Bu ester of lOa/lOb was dissolved in dichloro methane (20 mL) and TFA (5 mL) was added at 0 C. The reaction was stirred at room temperature overnight. The reaction was concentrated and dried under reduced pressure to give pure lOa/lOb.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOTIUM, INC.; MAO, Fei; MCGARRAUGH, Patrick, Gordon; MADRID, Alexis, Spain; LEUNG, Wai-Yee; ROBERTS, Lori, M.; (104 pag.)WO2016/69922; (2016); A1;,
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Related Products of 39503-58-7, These common heterocyclic compound, 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-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.

A solution of S2(12.8g, 48.8 mmol), N-bromosuccinimide (9.68 g, 54.78 mmol, 1.1 eq.), azobisisobutyronitrile (1.64 g, 9.96 mmol, 0.2 eq.) in carbon tetrachloride was heated at 70 C. After 14 h, solvent was removed and the residue purified by flash chromatography (Si02, 1 :9 ethyl acetate/hexanes) to afford S3 (13.92 g, 71.3 %) as a white amorphous solid. 1H NMR (500 MHz, CDC13) delta 7.91 (s, 1H), 7.60 (s, 1H), 7.00 (s, 1H), 3.99 (s, 3H), 3.90 (s, 3H).13C NMR (125 MHz, CDC13) delta 164.7, 159.0, 144.8, 135.5, 123.0, 114.6, 109.5, 56.7, 52.7, 39.3. HRMS (ESI+) m/z [M + H+] calcd for C10H11Br203, 336.9075, found 336.9079.

The synthetic route of 39503-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (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. 29823-21-0, name is Ethyl 8-Bromooctanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Ethyl 8-Bromooctanoate

a) 4,5-Bis(4-methoxyphenyl)-2-phenylimidazole (7 g) (J. Med. Chem., 1974, 17, 1182-8) and ethyl 8-bromo-octanoate (9.9 g) were reacted in a method similar to Example 9. Column chromatography on silica gel eluted with a hexane:ethyl acetate gradient gave 1-(7-ethoxy-carbonylheptyl)-4,5-bis(4-methoxyphenyl)-2-phenyl-imidazole (10.3 g, 100%) as an oil. NMR d (CDCl3) 0.8-1.5 (13H, m, 5*CH2, CH3), 2.18 (2H, t, CH2 =O), 3.75 (3H, s, OCH3), 3.88 (5H, m, NCH2, OCH3), 4.1 (2H, q, CH2 OC=O), 6.7-7.7 (13H, m, ArH) ppm.

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 29823-21-0.

Reference:
Patent; SmithKline Beecham Corporation; The Johns Hopkins University; US5648373; (1997); 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. 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

Place 5-bromo-2-methyl-benzoic acid (1.0 g, 4.7 mmol) in a 200 mL flask under an N2 atmosphere and add methanol via syringe. Add a 2M solution of diazomethyl- trimethyl-silane in hexane (3.5 mL, 23.0 mmol) drop wise over 10 minutes and stir for 1 hour at room temperature. Add glacial acetic acid (16 mL) and stir for 45 minutes. Dilute with ethyl acetate (100 mL) and wash with 1M aqueous sodium hydroxide solution (30 mL), saturated aqueous sodium bicarbonate solution (30 mL) and brine (30 mL). Dry the organic layer (Na2SO4), filter and concentrate in vacuo to obtain 1.01 g of 5-bromo-2- methyl-benzoic acid methyl ester (99 %). Place 5-bromo-2-methyl-benzoic acid methyl ester (1.04 g, 4.5 mmol) in a 50 mL flask under a N2 atmosphere and add carbon tetrachloride (15 mL). Add N-bromo- succinamide (1.49 g, 8.3 mmol) and 2,2′-azobisisobutyronitrile (40 mg, 0.2 mmol) and fit flask with a condenser and reflux for 4 hours. Cool to room temperature and filter. Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting with dichloromethane in hexane (0 to 50%) to obtain 977 mg of 5-bromo-2-bromomethyl-benzoic acid methyl ester (70%). Using 5-bromo-2-bromomethyl-benzoic acid methyl ester (0. 984 g, 3.20 mmol) and the procedure described in the I st paragraph for the alternative procedure for 5- (4,4, 5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) -2, 3-dihydro-isoindol-1-one, prepare 509 mg of the title compound (75 %).

According to the analysis of related databases, 79669-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); 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. 927-68-4, name is 2-Bromoethyl acetate, A new synthetic method of this compound is introduced below., Recommanded Product: 927-68-4

(1) Synthesis of (+-)-1-(2-acetoxyethyl)-2-oxocyclopentanecarboxylic acid methyl ester To a dry acetone solution (500 ml) containing 31.0 g (0.218 moles) of 2-oxocyclopentanecarboxylic acid methyl ester and 40.0 g (0.240 moles) of 2-bromoethyl acetate, 45 g (0.326 moles) of potassium carbonate was added to prepare a suspension, and the prepared suspension was stirred at 60C for 24 hours. After the suspension was cooled to the room temperature by leaving standing, the suspension was filtered. The filtrate was diluted with ethyl acetate (500 ml), washed with hydrochloric acid (0.1 mole/liter), water and a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified in accordance with the silica gel column chromatography using a hexane/ethyl acetate mixed solvent (the ratio of the amounts by volume: 3/1) as the elution solvent, and 34.8 g (0.152 moles) of (+-)-1-(2-acetoxyethyl)-2-oxocyclopentanecarboxylic acid methyl ester was obtained as a colorless transparent liquid substance. The yield was 70%. The analytical data of the obtained compound are shown in the following. FTIR (CHCl3): 2958, 1735, 1435, 1232 1H-NMR (400 MHz): 4.19 (dt, J=11.2, 6.8 Hz, 1H), one of -CH2OAc, 4.08 (dt, J=11.2, 6.8 Hz, 1H), one of -CH2OAc, 3.70 (s, 3H), -CO2CH3, 2.56 (ddd, J=12.6, 6.8, 2.0 Hz, 1H), one of -CH2-C=O, 2.45 (dd, J=6.8, 4.8 Hz, 1H); 2.41 (d, J=8.4, 4.8 Hz, 1H), 2.31 (dd, J=14.4, 6.8 Hz, 1H), 2.25 (dd, J=14.4, 8.4 Hz, 1H), 2.00 (s, 3H).-OCOCH3, 2.06-1.67 (m, 3H) 13C-NMR (100 MHz): 213.8 (C) carbon of ketone C=O, 170.8 (C) carbon of ester C=O, 170.6 (C) carbon of ester C=O, 60.9 (CH2) methylene carbon adjacent to OAc, 58.5 (C) quaternary carbon, 52.7 (CH3) methyl carbon of ester of CO2Me, 37.5 (CH2), 32.8 (CH2), 32.5 (CH2), 20.9 (CH3) methyl carbon of acetate, 19.7 (CH2) HRMS (EI): Calcd. for C11H16O5 (M+) 228.0998, Found: 228.0979

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; ZEON CORPORATION; EP1719746; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2216-92-4, name is N-Phenylglycine Ethyl Ester, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2216-92-4

Example 71 Synthesis of 3-(2-naphthylsulfonyl)-1-(phenyl)-imidazolidin-2,4-dione (Compound 71): In a similar manner to Example 70, 470 mg (1.28 mmol; yield: 26.6%) of the title compound were obtained as white crystals from 860 mg (4.83 mmol) of ethyl N-phenylamino-acetate and 1.39 g (81%, 4.83 mmol) of 2-naphthalenesulfonyl isocyanate. Melting point: 208-210 C. PMR (delta ppm, DMSO-d6): 4.52(s,2H), 7.1-8.3(m,11H), 8.76(s,1H).

According to the analysis of related databases, 2216-92-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suntory Limited; US5691335; (1997); A;,
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. 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 217314-47-1

To the solution of 1.57 g (8.7 mmol, 1 eq) 3-amino-5-methoxy-benzoic acid methyl ester (CAS 217314-47-1, can be prepared according to literature procedures) and 0.11 g (0.87 mmol, 0.1 eq) 4-dimethylaminopyridine in 18 ml THF is added the solution of 1.89 g (8.7 mmol, 1 eq) BOC-anhydride in 7 ml THF. The reaction mixture is stirred at rt over night. After dilution with EtOAc the mixture is washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, and the solvents are evaporated at reduced pressure. The residue is purified by chromatography on silica (flashmaster, hexane to hexane/EtOAc 7/3) to give 0.83 g (2.9 mmol, 34%) product as white solid.MS (LC/MS): 182=[M+H]+ 1H-NMR (400 MHz, CDCl3): 7.54-7.51 (m, 1H), 7.39 (br s, 1H), 7.29-7.28 (m, 1H), 6.59 (br s, 1H), 3.93 (s, 3H), 3.87 (s, 3H), 1.56 (s, 9H).

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; Betschart, Claudia; Lerchner, Andreas; Machauer, Rainer; Rueger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2008/132477; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 114312-57-1, A common heterocyclic compound, 114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, molecular formula is C10H11FO2, 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.

Add ethyl 3-fluoro-2-methylbenzoate (5.1g, 28mmol) to the reaction flask,N-bromosuccinimide (5.6g, 31mmol),Benzoyl peroxide (0.34g, 1.4mmol) and CCl4 (30mL).Under the protection of nitrogen, the temperature of the reaction solution was raised to 82C and the reaction was stirred for 17 hours.After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filter cake was washed with EtOAc (50 mL). The resulting filtrate was sequentially saturated sodium thiosulfate solution (100 mL×2),The citric acid solution (50 mL) and saturated brine (50 mL) were washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was vortexed under reduced pressure.The obtained crude product was purified using silica gel column chromatography (eluent: PE/EA (v/v) = 10/1),The title compound was obtained as a light yellow oil (6.17g, 84%).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Luo Huichao; Ren Qingyun; Yin Junjun; Wu Chunlin; Fan Yuxin; Mo Yufeng; Zhang Yingjun; (102 pag.)CN111057074; (2020); A;,
Ester – Wikipedia,
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Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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: Methyl 3-bromobenzoate

In a 25 mL round-bottomed flask, toluene (10 mL) was degassed with argon for 20 min. Under a flow of argon, Pd(OAc)2 (0.05 g, 0.23 mmol), BINAP (0.23 g, 0.37 mmol) and Cs2CO3 (2.12 mmol, 6.51 mmol) were added and left to stir for a further 20 min. To the mixture, methyl (3-bromobenzoate) 1 (1.01 g, 4.65 mmol) and aniline 2 (0.51 mL, 5.58 mmol) were added. The reaction was stirred at 120 C and monitored by thin layer chromatography (TLC) for 24 h. Upon completion, the reaction was cooled to room temperature and filtered through Celite, with hexane as the eluent, followed by concentration under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/ethyl acetate (90:10) (Rf 0.23) to afford 0.87 g (82%) of 3 as a pale yellow solid; M.p. 110-112 C (literature M.p. 110-111 C) [40]; 1H NMR (400 MHz/CDCl3)/ppm, delta = 3.90 (s, 3H,-COOCH3), 5.81 (s, 1H, -NH), 6.98 (app. t, 1H, app J = 8 Hz, CHparaC4H4-NH), 7.09 (app. d, 2H, CHparaC2H2metaC2H2ortho-NH), 7.23 (m, 1H, HN-CH-C(COOCH3)-CHCHCH-), 7.29 (m, 3H, C2H2ortho-HN-CH-C(COOCH3)-CHCHCH-), 7.57 (app. d, 1H, HN-CH-C(COOCH3)-CH), 7.72 (m, 1H, HN-CHC(COOCH3)); 13C NMR (100 MHz/CDCl3)/ppm, delta = 52.2, 118.2, 118.4, 121.5, 121.77, 121.80, 129.4, 129.3, 131.4, 142.4, 143.6, 167.1; Found [M+H]+ (C14H14NO2) m/z 228.1019 (Calc. 228.1025); IR (ATR) v/cm-1: 3358, 3030, 1694, 1578, 1294, 744.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 618-89-3, its application will become more common.

Reference:
Article; Higgins, Clare L.; Filip, Sorin V.; Afsar, Ashfaq; Hayes, Wayne; Tetrahedron; vol. 75; 51; (2019);,
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