Tag: M.W=200-300

1459-96-7, A common compound: 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step C. A mixture of the title compound from Step B above (20 g) and KOH (5.5 g) in MeOH/H2O (10:1, 106 mL) was heated to reflux overnight, cooled to room temperature and concentrated. The residue was diluted with EtOAc and extracted with IN aqueous NaOH (2 x 10O mL). The organic phase was dried (MgSO4), filtered and concentrated to give the starting material as a white solid. The combined aqueous phases were adjusted with 2N aqueous HCl to pH 1-2 and extracted with EtOAc (4 x 250 mL). The combined turbid organic phases were filtered through a fluted filter, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to give the title compound as a colorless solid (13.1 g, 70%). [MH]+ = 213.

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, Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63671; (2008); A2;,
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24398-88-7, 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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of ethyl-3-bromobenzoate (3.0 g, 13 mmol), [3-(hydroxymethyl)- phenyl]boronic acid (3.0 g, 20 mmol), PdCl2(PPh3)2 (0.46 g, 0.66 mmol), K2CO3 (3.6 g, 26 mmol), methanol (4 mL), and toluene (36 mL) was heated at 80 0C for 18 h under N2 and then allowed to cool to rt. The reaction mixture was filtered through Celite and then poured into a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted with ethyl acetate (x 3). The organic extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography to give ethyl 3′- (hydroxymethyl)biphenyl-3-carboxylate as an orange oil. A solution Of CBr4 (5.8 g, 17 mmol) and CH2Cl2 (20 mL) was added dropwise to a solution of the above alcohol, PPh3 (4.6 g, 18 mmol), and CH2Cl2 (50 mL) at 0 0C under N2. The reaction was allowed to warm to rt, maintained for 2 h, concentrated, and purified by silica gel chromatography to give ethyl 3′- (bromomethyl)biphenyl-3-carboxylate as a clear oil. Ethyl 3′-(bromomethyl)biphenyl-3- carboxylate was used to alkylate l-(2,2-dimethylpropyl)-4-propyl-lH-indol-5-ol following the procedure outlined in example 1. A mixture of the above indole (0.66 g, 1.4 mmol), 1 N LiOH (8 mL), and TEtaF (8 mL) was heated at 40 0C for 2 d and then cooled to 0 C- acetone can used in place of TEtaF if faster reaction rates are desired. The reaction was acidified to pEta = 1 with cone. HCl and extracted with ethyl acetate (x 3). The organic extracts were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography to give a yellow oil. 1H NMR (CDCl3, 500 MHz) delta 8.39 (s, IH), 8.11 (d, IH), 7.85 (d, IH), 7.76 (s, IH), 7.59- 7.48 (m, 4H), 7.12 (d, IH), 7.05 (d, IH), 6.96 (d, IH), 6.46 (d, IH), 5.16 (s, 2H), 3.84 (s, 2H), 2.95 (t, 2H), 1.76 (m, 2H), 1.01 (t, 3H), 0.99 (s, 9H). MS (ESI): 456 (M+H).

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/91496; (2006); A2;,
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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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 139102-34-4

1.936 kg (6.22 mol) of a 65% Red-Al solution in toluene were charged with 1.25 l of toluene at -5 C. To this solution was added 0.66 kg (6.59 mol) of 1-methylpiperazine, which was rinsed in with 150 ml of toluene, keeping the temperature between -7 and -5 C. The mixture was then left to stir at 0 C. for 30 minutes. This solution was then added to a solution of 1.261 kg (5.147 mol) of methyl 4-bromo-2-methoxybenzoate (XV), dissolved in 4 l of toluene, keeping the temperature at -8 to 0 C. After rinsing in twice with 0.7 l of toluene, the mixture was then stirred at 0 C. for 1.5 hours. For the work-up, the solution was added to cold aqueous sulphuric acid at 0 C. (12.5 l of water+1.4 kg of conc. sulphuric acid). The temperature should increase at maximum to 10 C. (slow addition). The pH was adjusted to pH 1, if necessary, by addition of further sulphuric acid. The organic phase was separated off and the aqueous phase was extracted with 7.6 l of toluene. The combined organic phases were washed with 5.1 l of water and then substantially concentrated and the residue taken up in 10 l of DMF. The solution was again concentrated to a volume of about 5 l. Determination of the content by evaporation of a portion resulted in a converted yield of 1.041 kg (94.1% of theory). The solution was used directly in the subsequent stage. HPLC method A: RT about 12.1 mm. MS (Elpos): mlz=162 [M+H]. 1H NMR (CDC13, 400MHz): oe=3.93 (3H, s), 7.17 (2H, m), 7.68 (1H, d), 10.40 (1H, s)

The synthetic route of 139102-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PLATZEK, Johannes; (30 pag.)US2018/244670; (2018); A1;,
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Some common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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. 252881-74-6

In a solution of tert-butyl 3- (2- (2- (2-aminoethoxy) ethoxy) ethoxy) propanoate (6.00 g, 21.64 mmol) and 3, 3′- ( (oxybis (ethane-2, 1-diyl) ) bis (oxy) ) dipropanoic acid (21.01 g, 84.00 mmol) in DMA (200 ml) were added EDC (18.00 g, 93.75 mmol) and DIPEA (5.00 g, 38.75 mmol) . The mixture was stirred overnight, then concentrated and purified by SiO 2 column chromatography (MeOH: CH 2Cl 2 = 1: 12 to 1: 5) to give the title compound as a white oil (9.15 g, 86%yield) . ESI m/z: calcd for C 23H 44NO 11 [M+H] +: 510.28, found: 510.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 252881-74-6, its application will become more common.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
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Some common heterocyclic compound, 105-76-0, name is Dibutyl maleate, molecular formula is C12H20O4, 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. 105-76-0

Example 2 Preparation of 3,6-dimethyl-2(3H)-benzofuranone by Means of Dehydrogenation Using Dibutyl Maleate as Hydrogen Acceptor A mixture of 1000 g of 5,6-dihydro-3,6-dimethyl-2(4H)-benzofuranone, 2000 ml of dibutyl maleate and 50 g of palladium-on-charcoal, 5% by weight, was heated for approx. 3 hours at 170 C. in an autoclave under autogenous pressure. After filtration, the product was purified by fractionating on an 80 cm packed column. Approx. 735 g of pure 3,6-dimethyl-2(3H)-benzofuranone were obtained at a b.p. of approx. 90 C. at 1 mbar.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105-76-0, its application will become more common.

Reference:
Patent; Haarman & Reimer GmbH; US6391365; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

252881-74-6, A common compound: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Compound C (11.5 mg, 20.2 mumol) and HATU (15.4 mg, 54.7 mumol) were dissolved in DMF (2 mL). DIPEA (35.2 muL, 202 mumol) and tert-butyl 12 amino-4,7,10-trioxadodecanoate (theoretical value 80%) (14.0 mg, ?40.3 mumol) were added to the obtained solution, and the obtained mixture was stirred in an argon atmosphere overnight at room temperature. The solvent was removed in a vacuum, and the residue was refined via HPLC (ODS-C18, A (water and 0.1% TFA):B (CH3CN and 0.1% TFA)=99:1 to 1:99; 20 minutes) to obtain a tert-butyl ester constituting Compound D in the form of a red amorphous solid (LRMS (ESI+): calculated [M+H]+ value: 827; measured value: 827).

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-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF TOKYO; Urano, Yasuteru; Nagano, Tetsuo; Asanuma, Daisuke; Hirose, Kenzo; Namiki, Shigeyuki; Takaoka, Yousuke; (28 pag.)US9784732; (2017); B2;,
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These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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. 1186-73-8

Step 2: Methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)- l-(2,4-dimethoxybenzyl)-4-hydroxy-9-methyl-2-oxo- 1,2,5, 6,7, 9-hexahydropyrido[3′,2′:6,7]cyclohepta[l,2-f]indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)- l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5(lH)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (10.6 g, 20.91 mmol) and trimethyl methanetricarboxylate (6.80 g, 35.76 mmol) were mixed together in Ph20 (40 mL). The stirred mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after initial bubbling of MeOH was observed (occurs at approx. 160 C internal reaction temperature). The reaction mixture was cooled to room temperature, loaded directly on a silica column, eluted first with hexanes to separate Ph20 and then anEtOAc/hexanes gradient (0-80%) to yield the product as a yellow foam (7.44 g, 56% 2 steps). LC-MS: 633.5 [M+H]+, RT 1.85 min. 1H NMR (500 MHz, CDC13) 5 ppm 0.08 (s, 3H), 0.09 (s, 3H), 0.90 (s, 9H), 1.45 – 1.55 (m, IH), 1.85 – 1.95 (m, IH), 1.96 – 2.05 (m, IH), 2.32 -2.44 (m, IH), 2.58 (dd, J=13.4, 6.1 Hz, IH), 2.96 (dd, J=13.4, 5.4 Hz, IH), 3.33 (s, 3H), 3.76 (s, 3H), 3.78 (s, 3H), 4.00 (s, 3H), 4.80 (s, 2H), 5.13 – 5.37 (m, 2H), 6.22 (d, J=2.2 Hz, IH), 6.28 (s, IH), 6.34 (dd, J=8.4, 2.2 Hz, IH), 6.81 (d, J=8.4 Hz, IH), 7.06 (s, IH), 7.32 (s, IH), 13.66 (br. s, IH)

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 1186-73-8.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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111-82-0, A common heterocyclic compound, 111-82-0, name is Methyl laurate, molecular formula is C13H26O2, 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.

laurateMethyl laurate (99.4%, 870 mg, Wako Pure Chemical Industries,Ltd.), Ru-Sn-Mo/C catalyst (43 mg), Fe (28 mmol (1564 mg)of 60-80 nm particles without previous activation), H2O(28-83 mmol), and tetradecane were introduced into a 100 mLHastelloy C high pressure reactor. After purging the reactor fourtimes with nitrogen, it was heated to the required temperatureand maintained at that state for 1-24 h. The stirring rate wasadjusted to 1000 rpm. The resulting products were separated bycentrifugation and filtration, and their yields were determinedby gas chromatography on an instrument equipped with a flameionization detector (Shimadzu, GC-2014) using anisole as aninternal standard. A capillary column (Restek, Stabilwax) wasused to analyze the esters, alcohols, acids, and higher molecularweight hydrocarbons. The conversion of methyl laurate and yieldof product were defined as follows:

The synthetic route of 111-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sagata, Kunimasa; Hirose, Mina; Hirano, Yoshiaki; Kita, Yuichi; Applied Catalysis A: General; vol. 523; (2016); p. 85 – 91;,
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148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-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.

N2Protected, 4-bromo-3-methylbenzoate (5mmol, 1.15g), 4- methoxycarbonyl phenyl boronic acid (5.1mmol, 0.92g), CsF (20mmol, 3.0g), a 100ml three-necked flask the Pd catalyst was added 5% (0.3 ~ 0.5g), 50ml of anhydrous THF as solvent, 67 deg.] C under reflux. after the reaction, the product was isolated by silica gel column chromatography (petroleum ether, dichloromethane) to give a pink solid 1.05g yield 74%

The synthetic route of Methyl 4-bromo-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Normal University; Dong, Yubin; Hu, Yuhong; Wang, Jiancheng; (12 pag.)CN106432087; (2017); A;,
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Ester – an overview | ScienceDirect Topics