Month: March 2021

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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, A new synthetic method of this compound is introduced below., Product Details of 609-12-1

Example 53N-Hydroxy-2-(4-methoxy-benzenesulfonyl)-3-methyl-butyramide 2-(4-Methoxy-phenylsulfanyl)-3-methyl-butyric acid ethyl ester was prepared according to the general method as outlined in Example 1. Starting from ethyl 2-bromo-3-methyl-butanoate (20.9 g, 100 mmol) and 4-methoxybenzenethiol (14.0 g, 100 mmol), 30 g of 2-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid ethyl ester was isolated. Yield 99%; Light yellow oil; MS: 269 (M+H)+.

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth Holdings Corporation; EP970046; (2003); B1;,
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Reference of 3618-04-0, 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 3618-04-0 as follows.

Step A: ethyl 4-(5 -bromopyridin-2-yloxy)cycl ohexanecarboxylateTo a solution of 5-bromo-2-hydroxypyridine (1.0 g, 5.747 mmol) and ethyl 4- hydroxycyclohexanecarboxylate (0.99 g, 5.75 mmol) in THF (50 mL) was added PPh3 (2.4 g,9.15 mmol) and DIAD (1.8 mL, 9.14 mmol). The reaction mixture was stirred at RT for 17 h.The solution was then concentrated and purified by silica gel column chromatography with anISCO system to yield ethyl 4-(5-bromopyridin-2-yloxy)cyclohexanecarboxylate as a colorless oil.

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; ASLANIAN, Robert; CAO, Jianhua; KIM, David; ZORN, Nicolas; WO2012/24179; (2012); 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. 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H10O3

10450] Step 1: To a nitrogen flushed vessel containing NaR (82 mg, 3.4 mmol), THF (6 mE) was added followed by the dropwise addition of methyl 3-hydroxycyclobutanecarboxy- late (0.360 mE, 3.4 mmol). The resulting suspension was allowed to stir at 0 C. for 35 mm. and then at RT for 45 mm. In a separate round bottom flask flushed with nitrogen, diisopropylamine (0.5 60 mE, 4 mmol) in THF (5 mE) was cooled to -78 C. before n-l3uEi (2.0 M in hexanes, 2 mE, 4 mmol) was added dropwise over 5 mm. The resulting solution wasallowed to stir at -78 C. for 30 mm. and then at 0 C. for 30 mm. The EDA thus generated was then added dropwise to the sodium alkoxide suspension at -78 C. Finally, ethyl iodide (0.320 mE, 4 mmol) was added and stirred at 0 C. for 15 mm and then at RT for 2.5 h. The crude mixture was quenched with sat. NH4C1 and extracted in ether. The combined organics were then washed further with brine, dried over Na2504, filtered and the filtrate concentrated in vacuo. Purification by way of column chromatography (5i02, 0-50% EtOAc/hexanes) afforded methyl 1 -ethyl-3-hydroxycyclobutanecar- boxylate. (277 mg, 51% yield).

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 4934-99-0.

Reference:
Patent; NOVIRA THERAPEUTICS, INC.; Chen, Austin; Bravo, Yalda; Stock, Nicholas; Pedram, Bijan; Jacintho, Jason; Clark, Ryan C.; (76 pag.)US2016/151375; (2016); A1;,
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Electric Literature of 175278-29-2,Some common heterocyclic compound, 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, molecular formula is C9H9FO2, 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: A mixture of methyl 3-bromo-2-methylbenzoate (500 mg, 3.3 mmol), NBS (770.4 mg, 4.3 mmol), and di-benzoyl peroxide (BPO, 80.7 mg, 0.3 mmol) in 1,2-dichloroethane (10 mL) was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over NaSO4, filtered and concentrated to give a crude product (683.2 mg, 89.6%), which was used in the next step reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-fluoro-2-methylbenzoate, its application will become more common.

Reference:
Article; Li, Qing; Meng, Liuwei; Zhou, Siru; Deng, Xiaoyan; Wang, Na; Ji, Yi; Peng, Yichun; Xing, Junhao; Yao, Gongmei; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 509 – 523;,
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Electric Literature of 15448-76-7,Some common heterocyclic compound, 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, molecular formula is C11H16O4, 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.

To a solution of dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate (2.00 g, 9.44 mmol, as prepared in Aust. J. Chem., 1985, 38, 1705-18) in MeOH (47 mL) was added KOH (0.475 g, 8.46 mmol) and water (2.5 mL). The reaction was stirred at reflux for about 16 h and then cooled to room temperature and concentrated to dryness under reduced pressure. Water (25 mL) was added to the remaining residue and the mixture was extracted with Et2O (2¡Á25 mL). The aqueous layer was acidified to about pH 4 using aqueous 6 N HCl and was extracted with DCM (3¡Á20 mL). The combined DCM extracts were dried over anhydrous MgSO4, filtered, and concentrated to provide 4-(methoxycarbonyl)bicyclo[2.2.1]heptane-1-carboxylic acid as an off-white solid (1.19 g, 71%): 1H NMR (400 MHz, DMSO-d6) delta 12.19 (s, 1H), 3.61 (s, 3H), 1.92 (d, J=6.6 Hz, 4H), 1.76 (s, 2H), 1.65-1.54 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; US2009/312338; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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, HPLC of Formula: C11H14O3

Preparation of Intermediate G-1. 10081] To a stirred solution of A-i (60 g, 309 mmol, 1 eq) and 1 -methylimidazole (30.4 g, 370 mmol, 1.2 eq) in CH2C12 (1 E) was added acetyl chloride (24.3 g, 309 mmol, 1 eq) at-45 C. under N2. After stirring for 20 mi TiC14 (210 g, 1.08 mol, 3.5 eq) and tributylamine (230 g, 1.24 mol, 4 eq) were added to the mixture at -45C. under N2, and continues to stir for 50 minutes at -45 C. under N2. Afier completion, water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over sodium sulfate. The solids were removed by filtration and the solvents of the filtrate were removed under reduced pressure. The crude was purified via silica column chromatography using a heptane to ethyl acetate gradient to afford a pale yellow oil, G-i.10082] ?H NMR (400 MHz, CHEOROFORM-d) oe ppm1.30 (t, J=7.2 Hz, 3H), 2.28 (s, 3H), 4.27 (q, J=7.2 Hz, 2H),4.41 (s, 1H), 4.58 (d, J=ii.8 Hz, 1H), 4.75 (d, J=i 1.8 Hz, 1H),7.32-7.43 (m, 5H)

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, Ethyl 2-(benzyloxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; McGowan, David; Raboisson, Pierr Jeane-Marie Bernar; Embrechts, Werner; Jonckers, Tim Hugo Maria; Last, Stefaan Julien; Pieters, Serge Maria Aloysius; Vlach, Jaromir; US2014/45849; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 609-12-1 as follows. category: esters-buliding-blocks

A mixture of 4,4-difluorocyclohexanone (1.00 g, 7.46 mmol), ethyl 2-bromo-3-methylbutanoate (1.56 g, 7.46 mmol), zinc powder (561 mg, 8.57 mmol) in dioxane (20 mL) is stirred at 85 oC for 2 days. After the removal of solvent, the filtrate is concentrated in vacuo. The residual oil is purified by column chromatography on silica gel eluting with 0-30% ethyl acetate in hexane to give the titled compound (1.46 g, 74% yield) as a pale yellow oil.

According to the analysis of related databases, 609-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAQUALIA PHARMA INC.; SHISHIDO, Yuji; OHMI, Masashi; ANDO, Kazuo; WO2015/136947; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 6290-49-9, 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. 6290-49-9, name is Methyl 2-methoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 1000 ml four-necked flask, 102 g (0.98 mol) of methyl methoxyacetate and 75 g (1.25 mol) of methyl formate were added, and the temperature was lowered to 10 C. with stirring.60 g (1.11 mol) of sodium methoxide was added in portions, and the temperature was controlled to not exceed 30 C.After the addition of sodium methoxide, the reaction was stirred at 25 C for 2h, and the temperature was raised to 36 C for 4h.At the end of the reaction, the temperature was lowered and suction filtered. The solid product content was 98.0%, and the yield was 92.0%.

The synthetic route of Methyl 2-methoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Kuai Da Agrochemical Co., Ltd.; Lin Longlong; Wu Feng; Cao Weidong; Xia Xiaofeng; (4 pag.)CN110759829; (2020); 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. 20602-77-1, name is 3-(Dimethylamino)propyl methacrylate, A new synthetic method of this compound is introduced below., Quality Control of 3-(Dimethylamino)propyl methacrylate

The first two steps to provide 2-chloro-l ,3,2-dioxaphospholane oxide were previously described and carried out according to the methods of Lucas7 and Edmundson 8.Methoxyethyl- l ,3,2-dioxaphospholane oxide was prepared as described in Example 1. The 3- (dimethylamino)propyl methacry.ate was synthesised according to the procedure described in Scheme II.3-(dimethylamino) propanol (0.02 mol) was blended in an oven dried round bottom flask, flushed with Ni, with anhydrous diethyl ether (60mL) and triethylamine (0.04 mol). The mixture was cooled down to -10C. Methacryloyl chloride (0.02 mol) in 7ml anhydrous diethyl ether was added dropwise to the reaction mixture over 30 min, maintaining the temperature at – 10C under N2. After the addition, the mixture was stirred and allowed to warm up slowly to room temperature overnight (20h). The triethylammonium chloride salt was filtered through celite and glass wool and washed thoroughly with diethyl ether. The solvent was removed via rotary evaporation and the product was purified by distillation under reduced pressure (40C at 0.5 mm Hg) to afford a yield of 75%. NMR (400 MHz, CDCI3) delta ppm: 1 .85 (dt, J=8 and J=8, 2H, -CH2-CHj-CH ), 1 .95 (s, 3H, CH3- C=CH2), 2.22 (s, 6H, -N(CH 2), 2.36 (t, J=8. 2Eta, -N-CH?-), 4.20 (t, J=8, 2Eta, -C/_ 0-C=0), 5.55 (d, J=4, 1Eta, Ci?=C-) and 6.10 (d, J=4, 1 Eta, CH2=C-) ; UC NMR ( 100 MHz, CDC13) delta ppm: 18.30 (CH3-C=CH2-), 27.00 (-CH2-CH2-CH2-), 45.47 (CH3-N-CH3), 56.30 (CH2-N-(CH3)2), 63.02 (-CH2- O-OO), 125.24 ( H2=C-), 136.43 (CH2=C-CH3).. 167.40 (0-C=0); FT-IR vmax / cm’ 1 : 2934 (CH3, CH2 St.), 1732 (0-C=0 st.), 1677 (C=C st), 1 154 (C-C-N bend), 1036 (C-O-C St.); ESI LCMS for C9H 1802N found m/z 172.1329 (M+H]+ (calculated 172.1338).The methoxyethyl-l ,3,2-dioxaphospholane oxide obtained ( 1 equivalent) was blended in an oven- dried glass bottle (SCHOTT Duran lOOmL) with previously synthesised 3-(dimethylamino)propyl meihacrylate ( 1 equivalent) and 2000 ppm of 2-methoxyphenol (Aldrich) with freshly distilled acetonitriie (2.6 molar). The mixture was stirred at 120C for 24 hours. At the completion of the reaction, most of the acetonitriie was removed in a stream of nitrogen. The remaining yellow/brown oil was dissolved in a minimum amount of anhydrous methanol and reprecipitated from anhydrous diethyl ether. This process was repeated 3 times. The crude oil was purified by silica gel column chromatography using a mixture of acetonitrile/methanoVwater in a ratio of 4/171 , respectively, yielding a transparent viscous oil. The oil was completely dried from water when dissolved in a small amount of acetoiiitrile and dried over MgS04 for 1 hour. The compound was dried under a stream of N and finally under high vacuum (yield = 46%). NMR (400 MHz. D20) delta ppm: 1.81 (s, 3H, CH,-OCH2-), 2.1 1 to 2. 18 (m, 2H, CH2-CV/ CH2-), 3.08 (s, 6H, CHjW-CHs), 3.28 (s, 3H, C fj-O-), 3.42 to 3.46 (m, 2H, -CJfc-N*-), 3.53 to 3.58 (m, 4H, -CH2-O and -CH2-N+-), 3.87 to 3.91 (m, 2Eta, -CH O-P=0), 4.16 to 4.18 (m, 4Eta, -CH O-P=0 and -CH2-0-C=0), 5.62 (d, J=4, Iota Eta, CH2=C-) and 6.03 (d, J=4, 1 Eta, CH2=C-); 31P NMR ( 162 MHz, D20) delta ppm: -0.32 ; l 3C NMR ( 100 MHz, D20) delta ppm: 17.27 (CH3-C=CH2-), 21.76 (CH CH2-CH2- ), 51.45 (CH3-N+-CW3), 58.06 (CH3-0-CH2-), 59.13 (-CH2-0-C=0), 61.85 (-CH2-0-P=0), 62.78 (- CHi-W-CH2-)t 64.67 (-CH2-N+-CH2-), 64.73 (-CH2-0-P=0), 71.46 (CH3-0-CH2-), 127.01 (CH2=C- ), 135.60 (CH2=C-CH3), 169.44 (O-OO); FT-IR vmax / cm’1 : 2959 (CH2 St.), 1717 (0-C=0 St.), 1637 (C=C st.), 1456 (-N^CH^ def.), 1298 (P=0 St.), 1239 (C-O-C St.), 1 160 (C-N bend), 1059 (P- O-C St.), 950 (-N(CH3)2 St.), 842 (CH2), 786 (CH2); ESI LCMS for C4H29NO7P found /z 354.1679 [M+H]+ (calculated 354.1682) and CMH2SN07PNa found m 376.1497 [M+Na]+ (calculated 376.1 501).

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; BIOINTERACTIONS LIMITED, UNIVERSITY OF READING; SANDHU, Shivpal, S.; RAISIN-DADRE, Fanny; MCKENDRICK, John, Ennis; RHODES, Alan; ONIS, Simon, Jon; WO2012/175923; (2012); A1;,
Ester – Wikipedia,
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Related Products of 99548-55-7, A common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

To a mixture of methyl 4-bromo-2-methylbenzoate (25.0 g) and (trifluoromethyl)benzene (400 mL) were slowly added N-bromosuccinimide (19.4 g) and 2,2?-azobis(isobutyronitrile) (1.79 g) at room temperature. The mixture was heated under reflux under nitrogen atmosphere at 80 C. for 18 hr, and cooled to room temperature. The insoluble substance was filtered off, the obtained filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (33.1 g). (1065) 1H NMR (300 MHz, DMSO-d6) delta 3.87 (3H, s), 4.99 (2H, s), 7.65-7.73 (1H, m), 7.78-7.84 (1H, m), 7.89 (1H, d, J=2.3 Hz)

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; Takeda Pharmaceutical Company Limited; KAIEDA, Akira; TOYOFUKU, Masashi; DAINI, Masaki; NARA, Hiroshi; YOSHIKAWA, Masato; ISHII, Naoki; HIDAKA, Kousuke; (155 pag.)US2017/15655; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics