Month: November 2020

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. 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, This compound has unique chemical properties. The synthetic route is as follows., 5616-81-9

Synthesis of (25,4a5,6a5,6bR, 8aR, 1OS,1 2a5, 1 2bR, 1 4bR)-Benzhydryl 1 O-(3 -((2-tert-butoxy-2- oxoethyl)(methyl)amino)-2-hydroxypropoxy)-2,4a,6a,6b,9,9, 1 2a-heptamethyl- 13 -oxo- 1,2,3 ,4,4a, 5,6,6a,6b,7,8,8a,9,1O,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (95-1). A solution of 82-2 (40 mg, 0.058 mmol) and tert-butyl sarcosine (46 mg, 0.32 mmol) in THF (0.50 mL) and water (0.10 mL) was heated at 65C for 5 hours. The reaction was concentrated to drynessand purified by flash chromatography (4g 5i02, 0-5% MeOHIDCM) to give the title compound (47 mg).

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Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
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Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. 609-12-1

General procedure: To a solution of sodium methoxide (prepared from 0.1mol of sodium in anhydrous MeOH (60mL)), 0.05mol of 1 and 0.055mol of ester (2a-h) were added and refluxed 1-3h (chromatographic control TLC). The solvent was evaporated and the residue was dissolved in water and neutralized with HCl to pH=7-8. The product was extracted with CHCl3, dried, concentrated, and crystallized from diethyl ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Article; Studzi?ska, Renata; Ko?odziejska, Renata; Kupczyk, Daria; P?azi?ski, Wojciech; Kosmalski, Tomasz; Bioorganic Chemistry; vol. 79; (2018); p. 115 – 121;,
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5788-17-0, A common heterocyclic compound, 5788-17-0, name is Methyl trans-3-methoxyacrylate, molecular formula is C5H8O3, 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.

4-Amino-5-[1-methoxy-2-(methoxycarbonyl)ethenyl]-7-(2-C- methyl-ss-D-ribofurnaosyl)-7H-pyrrolo [2,3-d]pyrimidine (13.1) [0191] To a solution of compound 11.2 (200 mg, 0.492 mmol) in 5 mL of anhydrous DMF were added Cul (19 mg, 0.2 eq. ), E-3-methoxymethacrylate (1. 06 mL, 20 eq.), triethylamine (137 7 LL, 2 eq. ) and Pd (PPh3) 4 (57 mg, 0.1 eq. ) at room temperature under an argon atmosphere. The reaction mixture was heated at 70C for 24 hr. then cooled to room temperature and 100 mL of 1/1 MeOH/CH2Cl2 was added. 400 mg Dowex 1×2-100 Bicarb form was then added and the suspension stirred at room temperature for 45 min. , then filtered. The resin was washed with 3X10 ML MEOH/CH2CL2 : 111. DMF was finally evaporated by azeotropic co-evaporation with toluene (2×5 mL). Chromatographic purification of the residue on silica gel (eluent: CH2CL2/MEOH : 95/5) gave 87 mg of product 13.1 (yield: 45%).

The synthetic route of 5788-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTA, INC.; WO2005/21568; (2005); A2;,
Ester – Wikipedia,
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455-68-5, A common heterocyclic compound, 455-68-5, name is Methyl 3-fluorobenzoate, molecular formula is C8H7FO2, 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: The oil was thendissolved in EtOH, and NH2NH2.H2O (3 eq) was added.The mixture was refluxed for 10 h. CH2Cl2 (30 mL) was thenadded and extracted with distilled H2O (3 ¡Á 20 mL). Theorganic phase was separated, dried on anhydrous Na2SO4,and evaporated under vacuum to afford correspondinghydrazide 7a in very good yield (white solid, 1.02g, 93percent)

The synthetic route of 455-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vu, Vu Van; Nhung, Trinh Thi; Thanh, Nguyen Thi; Chinh, Luu Van; Tien, Vu Dinh; Thuy, Vu Thu; Thi Thao, Do; Nam, Nguyen Hai; Koeckritz, Angela; Vu, Tran Khac; Journal of Chemistry; vol. 2017; (2017);,
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These common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, 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. 109232-37-3

5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (136 mg, 0.28 mmol) and isobutyl 5-chloro-2,2-dimethylpentanoate (124 mg, 0.56 mmol) are dissolved in DMA (1 mL) and Cs2C03 (183 mg, 0.56 mmol) and Nal (42 mg, 0.28 mmol) added. The mixture is microwaved at 150 C for 20 min then diluted with water and extracted with EtOAc (3 x20 mL). The organic is then washed with Brine (10 mL) and dried over Na2S04 and concentrated. HPLC purification gives 70 mg (38% yield) of alkylated product isobutyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6- yl)methylsulfonamido)-2,2-dimethylpentanoate. MS-ES [M + H]+ = 670.2. This compound is used directly in the next step.

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 109232-37-3.

Reference:
Patent; NOVARTIS AG; BARNES, David; CHOPRA, Rajiv; COHEN, Scott Louis; FU, Jiping; KATO, Mitsunori; LU, Peichao; SEEPERSAUD, Mohindra; ZHANG, Wei; WO2011/131709; (2011); A1;,
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25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 mixture of 4.203 g (25 mmol) of ethyl 4,4,4-trifluorocrotonate, 20 mL of nitromethane and ca. 0.576 g (5 mmol) of tetramethyl guanidine was stirred for 13 hours at room temperature, and then diluted with water and acidified by the addition of 0.5 M sulfuric acid. The mixture was extracted three times with diethyl ether. The combined ether extracts were washed with water, and then brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5.601 g (98%) of 4,4,4-trifluoro-3-nitromethyl-butyric acid ethyl ester as an amber oil.

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 25597-16-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Zhi; ERICKSON, Shawn David; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/60341; (2014); A1;,
Ester – Wikipedia,
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4224-69-5,Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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 stirred mixture of methyl 2-(bromomethyl)acrylate (239 mul, 2 mmol) in petroleum ether (3 ml) was added potassium carbonate (276 mg, 2 mmol), followed by sodium methoxide (119 mg, 2.2 mmol) and methanol (450 mul). The resulting mixture was stirred overnight, filtered, concentrated to a residue that was purified by column chromatography eluting with 10% ether in hexanes to provide the title compound (150 mg, 58%). (Reference: J. Med.Chem.; 42; 15; 1999; 2760-2773.)

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

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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. 4224-69-5

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4224-69-5, its application will become more common.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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 46064-79-3 as follows. 46064-79-3

Triethylamine (61 mg, 0.60 mmol) was added to a mixture of crude 2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (110 mg, 0.5 mmol) (from Example 18 supra) and HATU (0.23 g, 0.6 mmol) (Aldrich) in DMF (5.0 mL) at room temperature. The resulting mixture was stirred until clear solution was obtained (light brown). Methyl 3-amino-4-bromobenzoate (0.14 g, 0.6 mmol) (Oakwood) was added. The mixture was stirred for another 20 hours. Precipitate formed. Water (50 mL), aqueous saturated sodium bicarbonate solution (10 mL), and ethyl acetate (30 mL) were added. After thorough mixing, pale yellow precipitate was collected by filtration, washed with water and ethyl acetate and dried in vacuum oven. Residue was recrystallized from DMF-ethyl acetate-hexanes to give product as pale yellow crystals. (Yield 0.04 g, 18.5%).HR-MS (ES+) m/z Calculated for C17H14BrN4O5 ([M+H]+): 433.0142. Found: 433.0143.

According to the analysis of related databases, 46064-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
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2005-10-9, The chemical industry reduces the impact on the environment during synthesis 2005-10-9, name is 6H-Benzo[c]chromen-6-one, I believe this compound will play a more active role in future production and life.

2a (58.8 mg, 0.3 mmol), NaBH4 (17.1 mg, 0.45 mmol) and EtOH (3 mL) was added to a flask (10 mL) and stired for 6 h at room temperature. The reaction mixture was wished with CH2Cl2 (3 x5 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (10/1, V/V) as eluent to give pure 6. 4.4.1. 6H-benzo[c]chromen (6)Prepared from 6H-benzo[c]chromen-6-one; isolated as whitesolid (50.3 mg, 92%), m.p. 130-132 C; 1H NMR (500 MHz, CDCl3):d 7.52-7.50 (m, 1H), 7.42-7.40 (m, 2H), 7.29-7.26 (m, 2H), 7.12 (dd,J1 7.5 Hz, J2 1.5 Hz, 1H), 7.02-6.99 (m, 1H), 6.95 (d, J 8.5 Hz,1H), 4.48e4.42 (m, 2H); 13C NMR (125 MHz, CDCl3): d 152.9, 138.9,136.5,130.9,130.8,129.4,129.3,128.6,128.5,127.8,120.8,116.4, 63.7.

The chemical industry reduces the impact on the environment during synthesis 6H-Benzo[c]chromen-6-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui; Tetrahedron; vol. 73; 2; (2017); p. 154 – 163;,
Ester – Wikipedia,
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