Category: esters-buliding-blocks

Application of 91-44-1, A common heterocyclic compound, 91-44-1, name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one, molecular formula is C14H17NO2, 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 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 132 muL (0.90 mmol) of compound E-1 and stirring under blue light for 24 hours, compound H-2 was obtained with a yield of 95%.

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; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
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Related Products of 369-25-5,Some common heterocyclic compound, 369-25-5, name is Methyl 3,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Intermediate 9: Methyl 4-{(3S)-aminopiperidin-1-yl}-3-fluorobenzoate N -Methylpyrrolidone (40 ml) was added to methyl 3,4-difluorobenzoate (1.29 g, 7.5 mmol), and the mixture was stirred at room temperature. Intermediate 8 (2.6 g, 15.0 mmol) and sodium hydrogencarbonate (4.03 g, 48 mmol) were added thereto, and the mixture was stirred at 110C overnight. Water (70 ml) was added to thereaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: chloroform: methanol = 8: 2) to give the title compound (0.55 g, 29%).

The synthetic route of 369-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1227083; (2002); 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. 1186-73-8, name is Trimethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1186-73-8

A mixture of N-benzyl-2-chloro-6-isopropyl-3-(3-methoxypropoxy)-6,7-dihydroquinolin-8(5H)-imine (0.34 g, 0.85 mmol) and trimethyl methanetricarboxylate (0.491 g, 2.50 mmol) in diglyme (3 mL) was heated at 180 C in a microwave reactor for 45 min. The reaction mixture was concentrated under reduced pressure and the residue purified by normal phase SiCb chromatography (0-70 % EtO Ac/hexanes) to give methyl 1-benzyl-9-chloro-4-hydroxy-5-isopropyl-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydro-1,10-phenanthroline-3-carboxylate as a yellow oil (0.12 g, 27 %, m/z: 527 [M+H] observed). NMR (300 MHz, CDCl3): d 13.80 (s, 1H), 7.28 (s, 1H), 7.16-6.98 (m, 5H), 6.30-6.10 (m, 2H), 4.20-4.11 (m, 2H), 4.02 (s, 3H), 3.59 (t, J= 6.0 Hz, 2H), 3.37 (s, 3H), 3.01-2.96 (m, 1H), 2.89-2.75 (m,2H), 2.16-2.08 (m, 2H), 1.42-1.37 (m, 1H), 0.84 (d, J= 6.0 Hz, 3H), 0.78 (d, J= 6.0 Hz, 3H).

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
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24807-40-7, 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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-((4-((phenylmethyl)oxy)phenyI)methyl)-4-pentenoate(33.1); To a solution of lithium diisopropylamide (6.5 mL, 13.0 mmol, 2.0M in heptanelambdaTHF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was slowly added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (10 mL) and 1 ,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then allyl iodide (1.08 mL, 13.0 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL). The solvent was concentrated in vacuo, and the residue was disolved in EtOAc (100 mL) and washed with brine (2 x 25 mL) and then dried with Na2SO4. The product thus obtained was purified on a silica gel column, to give the title compound 33.1. 1H NMR (500 MHz, CDCl3) delta ppm 2.29 – 2.34 (m, 1 H) 2.39 – 2.44 (m, 1 H) 2.63 – 2.79 (m, 2 H) 2.91- 2.96 (m, 1 H) 3.64 (s, 3 H) 5.06 – 5.18 (m, 4 H) 5.67 – 5.85 (m, 1 H) 6.88 – 7.03 (m, 2 H) 7.03 – 7.18 (m, 2 H) 7.34 – 7.49 (m, 5 H).

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; AMGEN INC.; WO2008/130514; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 107582-20-7 name is Methyl 2,3-diaminobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 107582-20-7

Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35¡ãC.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10¡ãC. The solid was filtered, washed with 150 mlof water, and dried at 50-60¡ãC to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50¡ãC by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5¡ãC. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65¡ãC for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,3-diaminobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/15134; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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. 99548-54-6

< Step 2>; Methyl 3-bromo-2-methylbenzoate (4.67 g, 20 mmol) obtained in Step 1 and 100 mi of benzene were placed into a flask, and N-bromosuccinimide (4.37 g, 25 mmol) and 2,2′-azobisisobutylnitrile (0.336 g, 2 mmol) were added thereto. The resulting mixture was refluxed for 6 hours, cooled to 0 C , and filtered to remove precipitate. The resulting solution was washed successively with 10% sodium sulfite and saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed under a reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain methyl 3- bromo-2-(bromomethyl)benzoate (5.27 g (84%)).1H nuMR (300 MHz, CDCl3) delta 7.62 (d, IH, J = 7.9 Hz), 7.49 (dd, IH, J = 7.9, 0.9 Hz), 6.99 (t, IH, J= 7.9 Hz), 4.88 (s, 2H), 3.70 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/51417; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 27798-60-3, name is Methyl 2-Methoxyphenylacetate, I believe this compound will play a more active role in future production and life. 27798-60-3

(b) Sodium (590 mg) was dissolved in ethanol (45 mL) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.65 g, 12 mmol), followed by methyl 2-methoxyphenylacetate (4.7 g, 26 mmol) were added. The reaction mixture was refluxed overnight, the solvent was stripped and the residue was treated with water and then 2N HCl. The product was collected by filtration and recrystallized from ethyl acetate to afford 2.23 g of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 145-146 C.

The chemical industry reduces the impact on the environment during synthesis 27798-60-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sanofi Winthrop, Inc.; US5656629; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

85920-63-4, Name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 85920-63-4, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Acetyl-Meldrum?s acid (309 mg, 1.66 mmol) was added to a solution of the denosylated precursor from the preceding reaction (300 mg, 663 mumol) in dioxane (15 mL). The reaction was stirred for 90 min at 80 C. Then a solution of KOH in MeOH (0.1 M, 16.6 mL, 1.66 mmol) was added and stirring was continued for another 60 min at 80 C. The solvent was removed under reduced pressure and the residue separated between DCM and aqueous ammonium chloride. The aqueous phase was extracted twice with DCM and the combined organic layers were dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude product (347 mg), which yielded 16 (260, 80%) as a 1:1 mixture of diastereomers after chromatographic purification (DCM/MeOH 25/1). The diastereomers of a small sample were separated by semipreparative HPLC (ACN/H2O 70/30). Rf (DCM/MeOH 95/5): 0.45. (6aR,11aS,11bR)-N-tosyl-CPA 16a (cis-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.55 (s, 1H), 7.30-7.27 (m, 1H), 7.25 (d, J=8.2 Hz, 2H), 7.05 (d, J=7.3 Hz, 1H), 4.00 (d, J=10.9 Hz, 1H), 3.58 (dd, J=10.9, 6.0 Hz, 1H), 3.02 (dd, J=16.3, 5.8 Hz, 1H), 2.94 (dd, J=16.1, 11.7 Hz, 1H), 2.59 (Psidt, J=11.6, 5.9, 5.9 Hz, 1H), 2.49 (s, 3H), 2.36 (s, 3H), 1.67 (s, 3H), 1.58 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=194.3, 185.0, 175.4, 144.7, 135.6, 133.1, 129.8 (CH), 129.3, 128.4, 126.9 (CH), 125.5 (CH), 122.9 (CH), 120.6 (CH), 116.2, 111.6 (CH), 105.4, 70.7 (CH), 63.6, 52.4 (CH), 35.4 (CH), 26.1 (CH3), 26.1 (CH2), 24.4 (CH3), 21.5 (CH3), 19.8 (CH3); HR-ES-MS: m/z=513.1449 (calcd 513.1455 for C27H26N2NaO5S); IR: nu=3415, 1709, 1614 cm-1. (6aS,11aS,11bR)-N-Tosyl-CPA 16b (trans-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.2 Hz, 1H), 7.55 (d, J=1.7 Hz, 1H), 7.29 (Psit, J=7.8 Hz, 1H), 7.25 (d, J=8.1 Hz, 2H), 7.06 (d, J=7.3 Hz, 1H), 4.09 (d, J=10.7 Hz, 1H), 2.95 (Psidt, J=11.4, 1.7 Hz, 1H), 2.92 (dd, J=15.6, 4.6 Hz, 1H), 2.88 (dd, J=15.5, 11.8 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H), 2.32, (Psidt, J=11.8, 11.8, 4.6 Hz, 1H), 1.60 (s, 3H), 1.53 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=193.6, 185.6, 174.6, 144.7, 135.7, 133.7, 130.9 (CH), 129.9, 129.4, 126.9 (CH), 125.6 (CH), 121.3 (CH), 121.2 (CH), 118.0, 111.9 (CH), 105.3, 71.2 (CH), 62.1, 58.0 (CH), 38.4 (CH), 28.0 (CH3), 27.2 (CH2), 21.5 (CH3), 19.8 (CH3), 19.7 (CH3); HR-ES-MS: m/z=489.1497 (calcd 489.1490 for C27H25N2O5S); IR: nu=3362, 1611 cm-1.

Statistics shows that 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione is playing an increasingly important role. we look forward to future research findings about 85920-63-4.

Reference:
Article; Beyer, W.R. Christian; Woithe, Katharina; Lueke, Bettina; Schindler, Michael; Antonicek, Horst; Scherkenbeck, Juergen; Tetrahedron; vol. 67; 17; (2011); p. 3062 – 3070;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 115118-68-8 name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 115118-68-8

3-Oxo-cyclobutanecarboxylic acid; [1244] 3,3-Dimethoxy-cyclobutane-1,1-dicarboxylic acid diisopropyl ester (0.1 mmol, 30 g) was refluxed in 20% HCI aqueous solution for 60 h. Part of the HCI aqueous solution was evaporated under high vacuum and light brown color oil remained. The oil was dissolved by EtOAc and washed by brine. The organic layer was dried by NaS04, filtered, and evaporated under vacuum. The title compound was obtained as an off-white solid after recrystallization from chloroform.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2005/97800; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, 55666-43-8

Preparation in accordance with scheme 6. To a solution of 6-((2,6- dichlorobenzyl)oxy) -1,2,3, 4-tetrahydro-2, 7 -naphthyridine (80 mg; 0.259 mmol; 1 eq) in 10 mL acetonitrile were added tert-butyl 3-bromopropanoate (56.8 mg; 0.272 mmol; 1.05 eq) and triethylamine (131 mg; 1.29 mmol; 5 eq). The mixture wasstirred at RT overnight. The mixture was extracted with water/ethylacetate. The organic phase was washed with water, dried with MgSO4, and evaporated. The residue was purified by flash chromatography (4g silica gel; 3-10% MeOH in DCM) giving the product with a yield of 40 mg (0.09 1 mmol; 35.3%).

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, tert-Butyl 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics