Author: Jessica.F

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.

To a solution of 3-mercapto-5-trifluoromethyl-benzoic acid methyl ester (990 mg, 4.19 mmol) in acetonitrile (25 mL) were added N,N-diisopropylethylamine (1.08 g, 1.46 mL, 8.38 mmol) and tert-butyl 4-bromobutanoate (935 mg, 4.19 mmol, CAS RN 110611-91-1). The clear yellow solution was stirred at room temperature for 2.5 hours and then poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow liquid (1.27 g, 80%). MS (ESI+): m/z=379 ([M+]).

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; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Erickson, Shawn David; Mattei, Patrizio; Richter, Hans; US2013/267519; (2013); A1;,
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Synthetic Route of 46004-37-9, 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. 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-chloro-4-aminobenzoic acid, methyl ester (13.95 g) was suspended in a mixture of water (65 ml) and concentrated hydrochloric acid (15.7 ml). After stirring at room temperature for 10 minutes, the suspension was cooled to 0 C. A solution of sodium nitrite (5.71 g) in water (37 ml) was gradually added over 20 minutes, maintaining a reaction temperature of 0 C. After stirring at 0 C. for 35 minutes, the reaction mixture was partially neutralized by the addition of solid sodium carbonate (3.16 g) to afford a cold solution of the diazonium salt.

The synthetic route of Methyl 4-amino-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
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 721-63-1 as follows. Product Details of 721-63-1

General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H16O3

To a solution of ethyl 4-hydroxycyclohexanecarboxylate 2 (mixture of cis and trans) (2.5 g, 14.5 mmol) and imidazole (1.97 g, 29 mmol) in anhydrous DMF (20 mL), tert-butyldimethylsilyl chloride (2.63 g, 17.5 mmol) was added. After stirring overnight, Et2O (60 mL) and 1M aqueous HCl (60 mL) were added. After extraction with Et2O, the combined organic phases were washed with 1M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a TBS-protected alcohol as a colorless oil (4.14 g), which was used in the next step without further purification. To a solution of the former alcohol (4.14 g, 14.5 mmol) in THF (20 mL) and methanol (12 mL), lithium hydroxide (0.7 g, 29 mmol) was added. The mixture was then stirred at 60 C for 3 h. After removal of the solvents, water and Et2O were added and the aqueous layer was extracted with diethyl ether, cooled in an ice bath then acidified to pH=1 with 1M aqueous HCl. After extraction with ethyl acetate, the organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 50:50) to give the title compound 3 as a mixture of cis/trans isomers (3.48 g, 100% yield) as a colorless oil; deltaH (400 MHz, CDCl3) 10.84 (2H, m, 2*COOH), 3.89 and 3.56 (2*1H, 2*bs, 2*H-4), 2.41-2.18 (2H, m, 2*H-1), 2.10-1.83 (6H, m), 1.74-1.59 (4H, m), 1.58-1.23 (6H, m), 0.88 and 0.87 (2*9H, 2*s, 2*(CH3)3CSi), 0.05 and 0.03 (2*6H, 2*s, 2*(CH3)2Si); deltaC (100 MHz; CDCl3) 181.8 (2*COOH), 70.5 and 66.7 (2*C-4), 42.0 and 41.9 (2*C-1), 34.8 (2*CH2), 32.9 (2*CH2), 27.1 (2*CH2), 23.4 (2*CH2), 26.1 and 26.0 (2*(CH3)3CSi), 18.3 and 18.2 (2*(CH3)3CSi), -4.5 and -4.7 (2*(CH3)2Si).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zeinyeh, Wael; Radix, Sylvie; Terreux, Raphael; Chemelle, Julie-Anne; Walchshofer, Nadia; Tetrahedron; vol. 72; 27-28; (2016); p. 4032 – 4038;,
Ester – Wikipedia,
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63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, 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. Safety of cis-Methyl 3-hydroxycyclobutanecarboxylate

Triphenylphosphine (484 mg, 1 .85 mmol) was added to a solution of 2,5-difluorophenol (0.2 g, 1 .537 mmol) in tetrahydrofuran (1 .7 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (240 mg, 1 .85 mmol) was added, followed by DIAD (0.35 mL, 1 .8 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 10%-60% EtOAc-heptane gradient to give the title compound (236 mg, 63%). 1H NMR (400 MHz, CDCI3) delta 2.48-2.59 (m, 2 H), 2.76 (ddd, J = 14, 7, 4 Hz, 2 H), 3.16-3.26 (m, 1 H), 3.75 (s, 3 H), 4.90 (quin, J = 7 Hz, 1 H), 6.49-6.63 (m, 2 H), 7.02 (ddd, J = 10, 9, 5 Hz, 1 H); LC-MS (LC-ES) M+H = 243.

The synthetic route of 63485-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18595-18-1, 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Triethylamine (0.12 g, 1.12 mmol) was added to a mixture of crude 2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (0.22 g, 1 mmol) (from Example 18 supra) and HATU (0.43 g, 1.12 mmol) (Aldrich) in DMF (10 mL) at room temperature. Mixture was stirred until clear solution was obtained (light brown). 3-Amino-p-toluic acid methyl ester (0.2 g, 1.2 mmol) (TCI-US) was added. Mixture was stirred for another 18 hours. Precipitate was formed. Water (45 mL), saturated aqueous sodium bicarbonate solution (5 mL), and ethyl acetate (20 mL) were added. After thorough mixing, yellow precipitate was collected by filtration, washed with water and ethyl acetate and dried in vacuum oven. (Yield 0.25 g, 67.9%). Sample was recrystallized from DMF with trace amounts of water to give 3-[(2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-4-methyl-benzoic acid methyl ester as pale yellow crystals that contained trace amounts of DMF. (Yield 0.23 g, 62%).LR-LC/MS (APCi+) m/z [M+H]+ 369.

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

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 135484-83-2,Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 toluene 12mL solution of methyl 2-amino-4-bromobenzoate 1.2g were added 1-fluoro-4-iodobenzene 1.5mL, cesium carbonate 3.4g, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20g of pale yellow solid. 1H-NMR(DMSO-d6) delta value: 3.86(3H,s),6.94(1H,dd,J=8.6,1.7Hz),7.04(1H,d,J=1.7Hz),7 .24-7.35(4H,m),7.80(1H,d,J=8.6Hz),9.27(1H,s).

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-amino-4-bromobenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 87-13-8, These common heterocyclic compound, 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate, 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.

Aniline (2.733 mL, 29.99 mMol) was stirred in diethyl ethoxymethylenemalonate (6.063 mL, 30.00 mMol) at 120-130C for 16.5 hours. T.l.c. analysis (ethyl acetate cyclohexane, 1 : 1) showed the presence of one UV-active product (Rf 0.84) and complete consumption of both starting materials. Upon cooling down of the reactionsolution to room temperature, intermediate diethyl 2-((phenylamino)methylene)malonate 35 solidified (as dark yellow crystalline solid,7.899 g, quant.). M.p. 36-37C; HRMS (EIj: found 263.11531 [M] C14H17N04requires 263.11521; Vmax (thin film): 3265, 3184 (w, NH), 3050 (w, ArC-H), 2981,2936, 2904, 2871 (m, alkyl C-H), 1717 (s, 2 x intramolecularly hydrogen-bondedC=O conjugated with C=C), 1691 (s, C=C-NH), 1655 (s, C=N-), 1623 (s, aryl conjugated C=C), 1255 (s, C-N stretch) cm?; 6H (CD3CN, 500 MHz): 1.31 (3H, t, JCH3,CH2 7.1 Hz, CH3), 1.32 (3H, t, JCH3,CH2 7.2 Hz, CH3), 4.19 (2H, q, JCH2,CH3 7.2 Hz, CH2), 4.25 (2H, q, JCH2,CH3 7.1 Hz, CH2), 7.16 (1H, tt, JparaArH,metaArHs 7.4 Hz, JparaArH,orthoArHs 1.1 Hz, para-ArH), 7.20 (2H, dt, Jortho&-Hs,metaArHs 7.6 Hz,JorthoArHsparaArH 1.0 Hz, 2 x orthoArHs), 7.38 (2H, m, J 7.4 Hz, 2 x metaArHs), 8.48(1H, d, JCH,NH 13.8 Hz, CH-NH), 10.81 (1H, d, JNH,CH 13.6 Hz, CH-NI]); 6c(CD3CN, 125 MHz): 14.1, 14.2 (2 x CH3), 60.3, 60.6(2 x CH2), 93.9 (O=C-C-C=O),117.6(2 x orthoArCs), 125.1 (paraArC), 130.1 (2 x metaArCs), 139.8 (ArCquat-NH),151.9 (NH-CH), 165.6 (C=O), 168.8 (hydrogen bonded C=O).

Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.

Reference:
Patent; UCL BUSINESS PLC; SELWOOD, David; HOBBS, Adrian; WO2015/189560; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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, Formula: C8H7ClO4S

General procedure: To a solution of 23 (313 mg, 1 mmol) in DMF (1 mL), was addedtriethylamine (210 mg, 2.05 mmol), methyl 4-chlorosulfonyl benzoate27c (235 mg, 1 mmol) and 4-dimethylaminopyridine (10 mg). Themixture was stirred at rt for 4 h. The solvent was removed and the residuewas purified by a silica column with CHCl3 and MeOH to afford356 mg of 24f as a white solid in 75% yield. TLC Rf 0.13 (CHCl3/MeOH,40:1); 1H NMR (DMSO-d6) delta 1.25 (s, 9H, Piv), 2.61 (s, 3H, NCH3), 3.91(s, 3H, OCH3), 4.21 (s, 2H, NCH2), 6.28 (s, 1H, 5-H), 7.95 (d,J=8.0 Hz, 2H, Ph), 8.18 (d, J=8.0 Hz, 2H, Ph), 10.85 (s, 1H, exch,PivNH), 11.66 (s, 1H, exch, NH), 11.88 (s, 1H, exch, NH).

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:
Article; Xiang, Weiguo; Dekhne, Aamod; Doshi, Arpit; O’Connor, Carrie; Hou, Zhanjun; Matherly, Larry H.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 27; 23; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1459-93-4, 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 1459-93-4 as follows.

Methyl isophthalate (2.00 g, 11.1 mmol) was dissolved in THF (60 mL), and a 2.0 mol/L solution of dimethylamine (11.1 ml, 22.2 mmol) in methanol, EDC hydrochloride (4.27 g, 22.2 mmol) and 1-hydroxybenzotriazole monohydrate (3.40 g, 22.2 mmol) were added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate = 1:3) to afford methyl 3-(N,N-dimethylcarbamoyl)benzoate (2.30 g, 100 %).

According to the analysis of related databases, 1459-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1700856; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics