Category: esters-buliding-blocks

Application of 23426-63-3, The chemical industry reduces the impact on the environment during synthesis 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, I believe this compound will play a more active role in future production and life.

Example 12A Methyl-3,3-dicyano-2,2-dimethylpropanoate In THF (91 ml), 3 g (45.411 mmol) of malonic acid dinitrile was slowly added to 1.816 g (45.411 mmol) of sodium hydride (60% in mineral oil). Then 5.876 ml (45.411 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was stirred overnight at RT. Then a further 5.876 ml (45.411 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was heated overnight to 50 C. Then once again, 1.762 ml (13.623 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was heated for a further 4 h to 50 C. Saturated aqueous sodium hydrogen carbonate solution was then added to the mixture and it was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and evaporated to dryness. 8.9 g of raw product was obtained, and was purified by silica gel chromatography (cyclohexane-ethyl acetate 4:1). Yield: 6.47 g (85% of theor.) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.40 (s, 6H), 3.74 (s, 3H), 5.27 (s, 1H).

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-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; FOLLMANN, Markus; STASCH, Johannes-Peter; REDLICH, Gorden; GRIEBENOW, Nils; LANG, Dieter; WUNDER, Frank; HUeBSCH, Walter; LINDNER, Niels; VAKALOPOULOS, Alexandros; TERSTEEGEN, Adrian; US2013/338137; (2013); A1;,
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Reference of 82702-31-6, 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

12a In accordance with a method known from the literature, methyl 3-bromo-4-fluorobenzoate is reacted, under (Ph3 P)2 PdCl2 catalysis, with (trimethylsilyl)acetylene to form methyl 4-fluoro-3-(2-trimethylsilylethinyl)benzoate. MS (ES): 251 (M+1).

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 3-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst Aktiengesellschaft; US5679712; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Quality Control of Methyl 4-chlorosulfonylbenzoate

Example 5-10b Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate To a solution of methyl 4-(chlorosulfonyl)benzoate (Example 5-10c) (4 g, 17.09 mmol) in dichloromethane (40 mL) at 0 C. in an ice bath, was added (4-methoxyphenyl)methanamine (2.56 mL, 19.65 mmol) and triethylamine (2.38 mL, 17.1 mmol). The ice bath was then removed and the mixture was allowed to warm to ambient temperature with stirring for an additional 2 hours. Upon completion (monitored by TLC 40% ethyl acetate/hexanes), the solvent was removed in vacuo. The residue was re-dissolved in ethyl acetate (200 mL), washed with 1N HCl (aq, 20 mL), water (20 mL) and brine (20 mL) then dried over magnesium sulfate. The solution was concentrated and the product purified by re-crystallization with hot ethyl acetate/hexanes to afford pure methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (4.3 g, 74.8%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta, ppm: 3.67 (s, 3H), 3.78 (s, 3H), 3.93 (s, 2H), 6.78 (m, 2H), 7.09 (m, 2H), 7.87 (m, 2H), 8.08 (m, 2H), 8.25 (br, s, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Senomyx, Inc.; US2009/274632; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 17994-94-4, name is Methyl 7-aminoheptanoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 7-aminoheptanoate hydrochloride

Methyl 7-(4-(2-oxo-2-(quinolin-8-ylamino)ethyl)benzamido)heptarioate, 69.; Compound 68 (200 mg, 0.65 mmol) was dissolved in CH2CI2 (20 mL) under argon. To this added 7-aminoheptanoic acid methyl ester (as the hydrochloride, 140 mg, 0.72 mmol), Et3N (73 mg, 0.72 mmol) and EDC (138 mg, 0.72 mmol) and the mixture was allowed to stir overnight at it. Added water and worked up with CH2CI2, the residue purified through flash column (silica gel 230-400 mesh, 80% ethyl acetate in hexanes) to ohtain 69 as white solid (238 mg, 82%). NMR (400 MHz, CDC13): S = 1.35-1.37 (m, 4 H), 1.58-1.64 (m, 4 H), 2.29 (t, 2 , J = 7.2 Hz), 3.43 (q, 2 H, J = 6.8 Hz), 3.64 (s, 3 H), 3.92 (s, 2 H), 6.18 (s, 1 H), 7.41-7.51 (m, 5 H), 7.77 (d, 2 H, J = 8 Hz), 8.15 (d, 1 H, J = 8 Hz), 8.71-8.73 (m, 2 H), 9.95 (s, 1 H). I3C NMR (75 MHz, CDC13): delta = 24.7, 26.5, 28.6, 33.8, 39.9, 44.7, 51.3, 116.3, 121.6, 121.8, 127.0, 127.6, 127.7, 129.4, 133.7, 134.0, 136.2, 137.9, 138.1, 148.2, 167.3, 168.9, 174.1 LRMS Calcd for C26H29N3O4: 448.21 Found: 447.90.

The synthetic route of 17994-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; BRESLOW, Ronald; MARKS, Paul, A.; ABHILASH, K., G.; WANG, Jianing; WO2011/146855; (2011); A1;,
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Electric Literature of 90942-47-5, A common heterocyclic compound, 90942-47-5, name is Methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride, molecular formula is C9H11Cl2NO2, 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 solution of methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride (1.80 g, 6.00 mmol) in THF (20 mL) were added DIPEA (3.096 g, 24.0 mmol) and pivaloyl chloride (1.2 mL, 9.0 mmol). The reaction mass was stirred at rt for 2 h, diluted with EtOAc and was washed with water, and brine. The organic layer was separated, dried, filtered and concentrated to afford 2.0 g of the title product. 1H NMR (300 MHz, DMSO-i): delta 8.16 (m, 1H), 7.65 (s, 1H), 7.53 (d, J = 8.4 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H), 4.25 (d, J = 5.7 Hz, 2H), 3.85 (s, 3H), 1.15 (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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2014/167444; (2014); A1;,
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Reference of 15964-79-1, A common heterocyclic compound, 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, molecular formula is C11H14O4, 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: 1.4mmol of 5-amino-1-substituted-4-carboxamide-1H-imidazole (1) was dissolved in 10mL of absolute methanol. Then 5.6mmol of the appropriate ester isadded into this solution. This mixture was added in 10mL ofmethoxide-methanol solution prepared from sodium (0.15 g, 6.3mmol) and 10mL of absolute methanol. The mixture was refluxed for 15-20 h. After cooling, the solvent was evaporated off and the residue was taken into ethyl acetate. The organic phase was dried over Na2SO4 and evaporated. And the residue was purified via silica gel chromatography(eluent: the mixture of ethyl acetate and methanol) to obtainthe pure product (2a-2q).

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Wei; Zhao, Xin-Yun; Chen, Xi; Zhan, Chang-Guo; Journal of Chemistry; vol. 2016; (2016);,
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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. 5616-81-9, name is tert-Butyl 2-(methylamino)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 2-(methylamino)acetate

A mixture of 2-chloromethyl-8-nitropyridine, (10 mmol), sarcosine t-butyl ester (11 mmol) and finely ground anhydrous potassium carbonate (30 mmol) in ethylene glycol dimethyl ether (DME) (20 mL) is heated under reflux for 8 hours. The reaction mixture is filtered hot and solid is washed with 30 mL of DME. The filtrate is evaporated in vacuo and the crude product is purified by recrystallization or chromatography to give 2-(N-methyl-N-t-butoxycarbonylmethyl)methyl-8-nitroquinoline.

The synthetic route of 5616-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bioflexis, LLC; US2006/94755; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. Formula: C9H9BrO2

Method A; Step e: 1-(3-bromophenyl)-2-pyridin-4-ylethanone; To 66 ml (0.066 mol) of sodium 1,1,1,3,3,3-hexamethyldisilazane 1M in THF under nitrogen atmosphere at 00C, 3.2 ml (0.033 mol) of 4-picoline were added. After stirring for 60 minutes 5 ml (7.15 g; 0.03 mol) of ethyl 3-bromo benzoate were added and the mixture maintained in the same conditions for 1.5 hours. HCI 2N was then added, the mixture made basic with NaOH 2N and extracted with ethyl acetate. The organic phase was dried over Na?SCM and the solvent evaporated. 7.5 g (82% yield) of the title compound were obtained by crystallization from AcOEt-Et2U. 1H NMR (401 MHz, DMSO-d6) delta = 8.52 (d, J = 6.0 Hz, 2 H), 8.19 (t, J = 1.7 Hz, 1 H), 8.05 (ddd, J = 1.0, 1.6, 7.8 Hz, 1 H), 7.89 (ddd, J = 1.0, 2.0, 8.0 Hz, 1 H), 7.54 (t, J = 7.9 Hz, 1 H), 7.19 – 7.33 (m, 2 H), 4.53 (s, 2 H). MS-ESI (M+H) calc. 276.0019 found 276.0023 (C13HIOBrNO)

The synthetic route of Ethyl 3-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PULICI, Maurizio; ZUCCOTTO, Fabio; BADARI, Alessandra; NUVOLONI, Stefano; CERVI, Giovanni; TRAQUANDI, Gabriella; BIONDARO, Sonia; TRIFIRO’, Paolo; MARCHIONNI, Chiara; MODUGNO, Michele; WO2010/10154; (2010); A1;,
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Related Products of 72594-86-6,Some common heterocyclic compound, 72594-86-6, name is Benzyl tert-butyl malonate, molecular formula is C14H18O4, 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.

EXAMPLE 5 2-(2-Methylthioethyl)propenoic acid benzyl ester Sodium hydride (0.96 g, 50percent suspension in mineral oil) was added to a stirred solution of t-butyl benzyl malonate (5 g) in dry dimethylformamide (50 ml), maintained at 0°C under an atmosphere of nitrogen. After stirring for 15 minutes, 2-chloroethyl-methyl sulphide (2.21 g) in dimethylformamide (10 ml) was added dropwise, while the temperature of the reaction was maintained below 10°C. The reaction was allowed to warm to room temperature and stirred for 15 hours when water was cautiously added. The reaction mixture was extracted with ethyl acetate (2 x 100 ml), the ethyl acetate extracts were washed with water (4x), dried (Na2SO4) and evaporated to give 4-methylthio-2-t-butyloxycarbonyl-butanoic acid benzyl ester as an oil (6.4 g).

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

Reference:
Patent; Pfizer Limited; EP274234; (1991); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1260092-46-3, 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. 1260092-46-3, name is tert-Butyl 3-(2-aminoethoxy)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of pomalidomide analogue (1 eq.), amine (1 eq.), and /V,/V-diisopropylethylamine (1.5 eq.) in DMF (2.0 ml per mmol of pomalidamide) was heated to 85 C in a microwave reactor for 40 min. After cooling to RT, the reaction was quenched with water and extracted with ethyl acetate (3X). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluted with hexanes/EtOAc: 0-100%) to give the desired /-Bu ester intermediate as oil. This intermediate was treated with a solution of hydrogen chloride in dioxane (4 M, 5 ml per mmol of pomalidamide) for overnight. After concentration under reduced pressure, the desired acid product was obtained as yellow oil.:_Synthesis of Intermediate 8. (0887) (0888) 3-(2-((2-(2,6-Dioxopiperidin-3-yl)-l,3-dioxoisoindolin-4-yl)amino)ethoxy) propanoic acid. /e/V-Butyl 3-(2-aminoethoxy)propanoate (1.0 g, 5.3 mmol) was used to prepare the title compound (500 mg, 24%) according to the above procedures. NMR (600 MHz, CD3OD) 5 7.54 (dd, = 8.3, 7.0, 1.2 Hz, 1H), 7.09 (d, 1H), 7.04 (d, .7= 7.0, 1.1 Hz, 1H), 5.05 (dd, 12.5, 5.4, 1.2 Hz, 1H), 3.75 (t, J= 6.2, 1.2 Hz, 2H), 3.65-3.69 (m, 2H), 3.45-3.49 (m, 2H), 2.88 – 2.82 (m, 1H), 2.76 – 2.70 (m, 2H), 2.56 (t, J= 6.2, 1.2 Hz, 2H), 2.10 (ddt, J= 14.9, 7.6, 3.7, 1.6 Hz, 1H). MS (ESI) m/z 390.2 [M+H]+.

The synthetic route of tert-Butyl 3-(2-aminoethoxy)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; JIN, Jian; LIU, Jing; SHEN, Yudao; GUCCIONE, Ernesto; WALSH, Martin; BOSCH, Almudena; SCHWARZ, Megan; (0 pag.)WO2019/165189; (2019); A1;,
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