Month: June 2021

These common heterocyclic compound, 140-11-4, name is Benzyl acetate, 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. Quality Control of Benzyl acetate

General procedure: Bioreactor cultures and biotransformations using E. coli JM109(pDTG601). Growth and biotransformation in the bioreactor usingE.coli JM109 (pDTG601) were carried out using a modification ofour previously published procedure.3b Thus, 5 mL of LB mediumsupplemented with ampicillin sodium salt (0.1 g/L) and glucose(5 g/L) were inoculated with a single colony of E. coli JM109(pDTG601), and grown overnight at 37 C and 150 rpm. Two500 mL shake-flasks containing 150 mL of MSB medium wereinoculated with 1 mL of the grown culture. These precultureflasks were placed in an orbital shaker at 37 C and 150 rpm, for12 hrs. Both entire cultures were used to inoculate the bioreactor(Sartorius Biostat A plus), charged with an initial volume of 2.5 L,and set to 500 rpm, 30 C, and air flow rate of 4L/min. The pHvalue was controlled automatically to 6.8 by addition of conc.ammonium hydroxide during the whole process. A pulse ofantifoam agents (Aldrich?s Antifoam Y: Silicone dispersion inwater 1:1) was added at the beginning of the run. At 6 h afterinoculation the dissolved oxygen value sharply increased(indicating carbon deprivation), whereupon a glucose fed-batchwas started by adding glucose (0.7 g/mL solution) from an initialrate of 0.08 mL/min to 0.54 mL/min in a 20 h period. When thebiomass concentration reached 15 g/L cdw, IPTG was added toinduce toluene dioxygenase expression (IPTG final concentrationin bioreactor of 10 mg/L), and the stirrer speed was set to900 rpm. After the culture reached the stationary phase (c.a.26 h, 50 g/L cdw aprox), glucose feeding was decreased to0.25 mL/min and substrate addition was started. A solution of thecorresponding substrate in liquid paraffin (0.5 M) was added at aflow rate of 20 mL/min using a peristaltic pump. After thebiotransformation was completed, the pH of the medium in thebioreactor was adjusted to 7.5. The culture broth was centrifugedat 7000 rpm and 4 C for 30 min, the supernatant was collectedand the cell pellet properly disposed. Centrifugation led to theseparation of the liquid paraffin (which contains no detectableamounts products) from the aqueous phase. The latter wasproperly lyophilized overnight to obtain a dry powder, whichwas extracted several times with ethyl acetate until no morediols were detected by TLC. The solvent was evaporated to affordthe corresponding diol, which was washed several times withhexanes to remove the liquid paraffin traces.

The synthetic route of Benzyl acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pazos, Mariana; Martinez, Sebastian; Vila, Maria Agustina; Rodriguez, Paola; Veiga, Nicolas; Seoane, Gustavo; Carrera, Ignacio; Tetrahedron Asymmetry; vol. 26; 24; (2015); p. 1436 – 1447;,
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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. 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;,
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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. 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;,
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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,
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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;,
Ester – Wikipedia,
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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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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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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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Reference of 174403-69-1, 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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of pyrazole (100 mg, 1.47 mmol), methyl 4-fluoro-2-methylbenzoate (123.51 mg, 0.73 mmol) and potassium carbonate (609.0 mg, 4.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 60 C for 16 h. The reaction was poured into water (5 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL x 2) and brine (10 mL), dried over Mg504 and concentrated. The residue was purified by prep-TLC (33% ethyl acetate in petroleum ether, Rf = 0.3) to afford methyl 2-methyl-4-(1H-pyrazol-1-yl)benzoate (50 mg, 15.7% yield) as a white solid. LCMS (Method 5-95AB): tR =0.732 mi [M + Hj = 216.9.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-fluoro-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
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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. 4385-35-7, name is 3-Isochromanone belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4385-35-7

To a suspension of isochromanone (99% pure, 149.7 g, 1.00 mol) in methanol (280 mL) was added dropwise over a period of 90 min at 14-16 C. sodium methanolate (30% in methanol, 270.0 g, 1.50 mol) and the resulting mixture was stirred for 90 min at 15 C. To this mixture was added dropwise over a period of 6.5 h at 9-13 C. iso-butyl nitrite (94% pure, 137.1 g, 1.25 mol) and the mixture was stirred at 8 C. overnight. The conversion was monitored by HPLC. After completion of the reaction, 4 M hydrochloric acid was added to adjust a pH<1 before the resulting suspension was stirred for overnight at 4 C. The crude product was collected by filtration, washed with cold dist. water (2×500 mL) and dried in vacuo at max. 45 C. Isochroman-3,4-dione-4-oxime was obtained as a colorless solid (145.9 g, 90.4 HPLC-area %, 74% yield).1H-NMR (DMSO-d6): delta=13.3 (s, 1H), 8.34 (d, J=7.4 Hz, 1H), 7.54-7.41 (m, 3H), 5.46 (s, 2H) ppm; 13C-NMR (DMSO-d6): delta=162.3, 140.2, 133.2, 130.2, 129.0, 127.9, 125.4, 125.0, 68.3 ppm; mp=179-182 C. The synthetic route of 4385-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASE SE; US2011/295022; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics