Esters-buliding-blocks

6933-47-7, Name is Methyl 4-amino-2-methylbenzoate, 6933-47-7, 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.

A solution of 143 3,5-dichloro-4-ethoxybenzoic acid (7: R1=Et) (285mg, 1.21mmol) and 144 DIPEA (1.05mL, 6.05mmol) in 35 DMF (2.5mL) was added to 38 HATU (690mg, 1.82mmol) and the orange mixture was stirred for 5min prior to the addition of 145 methyl 4-amino-2-methylbenzoate (8: R=R2=Me) (200mg, 1.21mmol) in DMF (1mL). The resulting dark orange solution was stirred for 18h. 2M 117 HCl (10mL) was added and stirring continued for 10min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3¡Á15mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40g, 0-100% 45 EtOAc in 136 isohexane) to afford 146 methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (10: R1=Et, R=R2=Me) (267mg, 56%): 1H NMR (400MHz, CDCl3) delta 7.97 (d, J=8.5Hz, 1H), 7.81 (2H, s), 7.83-7.77 (1H, m), 7.59-7.48 (2H, m), 4.18 (2H, q, J=7.0Hz), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t, J=7.0Hz). m/z 380 (M-H)- (ES-).

Statistics shows that Methyl 4-amino-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 6933-47-7.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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619-42-1, 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 619-42-1 as follows.

EthynyHrimethylsilane (82.4 g. 0.84 rnol. 1.2 equiv) was added dropwise over 10 min under a nitrogen atmosphere to a soiution of methyl 4-brornobenzoate (150 g, 0.7 mol 1.0 equiv), PdC2 iPP h), (15 g, 0.021 mot.. 0.03 equiv) and Cul (13 g, 0.068 mol, 0.1 equiv) in TEA (1.5 L), The reaction was stired at 90C for 30 minutes, whereupon LCMS showed complete consumption of methyl 4-bromobenzoate. Then, the reaction mixture was filtered and the filter cake was washed with EiOAe (5 x 500 rnLj, The filtrate was concentrated under reduced pressure to give a residue, which was distilled under reduced pressure to yield methyl 4~{{triroethyi8tiyi) ethynyl) benzoate (INT-1.2) as an off-white solid (156 g, 96%).

According to the analysis of related databases, Methyl 4-bromobenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian, D.; LU, Qing; AGGEN, James, Bradley; DOZZO, Paola; KASAR, Ramesh, Annasaheb; LINSELL, Martin, Sheringham; KANE, Timothy, Robert; GLIEDT, Micah, James; HILDEBRANDT, Darin, James; MCENROE, Glenn, A.; COHEN, Frederick; WO2013/170030; (2013); A1;,
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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. 13671-00-6, name is Methyl 2,6-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 13671-00-6

To 30 ml of a THF solution containing 700 mg of 2-(2-chloropyridin-3-yl)acetic acid was added dropwise 7.75 ml of a 1.9 mol/L THF solution of hexamethyldisilazane sodium at -78 C. and the mixture was stirred for 10 minutes. Then, 616 mul of methyl 2,6-difluorobenzoate was added dropwise thereto, and then, the temperature of the mixture was raised from -78 C. to room temperature and stirred for 1 hour. To the mixture was added an aqueous saturated ammonium chloride solution followed by stirring the mixture for 1 hour. Thereafter, ethyl acetate was added thereto and the liquids were separated. The obtained organic layer was washed with saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 450 mg of a transparent oily product. (1215) 1H-NMR (CDCl3) delta: 8.35 (1H, dd, J=4.7, 1.8 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.44-7.43 (1H, m), 7.25 (2H, dd, J=7.6, 4.7 Hz), 7.00-6.96 (2H, m).

The synthetic route of 13671-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; OKAYA, Shun; IKISHIMA, Hideaki; FUKUMOTO, Takeshi; NISHIDA, Akihiro; YANAGI, Masanori; NAITO, Ryohei; MASUTOMI, Koji; SHIRAKAWA, Tomomi; SAKURADA, Akane; YUTANI, Satoshi; (368 pag.)US2020/45968; (2020); A1;,
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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. 1128-76-3, name is Ethyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1128-76-3

General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a.

The synthetic route of 1128-76-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maekawa, Hirofumi; Okawara, Hikaru; Murakami, Taro; Tetrahedron Letters; vol. 58; 3; (2017); p. 206 – 209;,
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110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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.

Exemplification of General Procedure J:; Preparation of tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)- lH-indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 ml) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert-butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 500C. After about 24h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5- yl)-lH-indol-l-yl)butanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LCMS (Table 1, Method c) Rt = 3.50 min, m/z 496 (M+H)+.

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 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/76356; (2008); 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. 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).

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; 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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