Category: esters-buliding-blocks

Reference of 1128-00-3, 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. 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-Pentynoic acid (15) (1.00 g, 10.19 mmol) in DCM (20 ml) under argon atmosphere at rt was treated with DMF (39 ll,0.51 mmol) and oxalyl chloride (2.22 ml, 25.48 mmol). The mixture was stirred for 40 min and the volatiles were evaporated. The residue was dissolved in DCM (3 ml) and the obtained solution was added to a mixture of ethyl 2-aminocyclohex-1-ene-1-carboxylate(0.10 g, 0.59 mmol) and DIPEA (1.76 ml, 10.2 mmol) in DCM (15 ml) at 5 C to 2 C under argon atmosphere. The mixture was stirred for 1 h at 0 C and warmed to rt. The mixture was diluted with DCM, washed with saturated NH4Cl, brine, and dried over Na2SO4. The solvent was evaporated and the residue was chromatographed on silica gel (EtOAc in petroleum ether, 1:20 to1:10) to afford a white solid. Recrystallization from n-heptane gave the product 18 (1.20 g). The filtrate after crystallization was concentrated and the residue was chromatographed on Biotage (EtOAcin petroleum ether, 2-20%) to give the product (0.25 g); the combined yield was 1.45 g, 57%. 1H NMR (300 MHz, CDCl3) d: 11.66(s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.03-2.92 (m, 2H), 2.65-2.49 (m,4H), 2.36-2.25 (m, 2H), 1.97 (t, J = 2.3 Hz, 1H), 1.70-1.54 (m, 4H),1.30 (t, J = 7.1 Hz, 3H). 13C NMR (75 MHz, CDCl3) d: 170.1, 169.6,152.1, 104.9, 82.8, 69.2, 60.4, 37.2, 28.7, 24.3, 22.0, 21.8, 14.6,14.4. LCMS (ESI) m/z 250.18 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-aminocyclohex-1-enecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4314 – 4329;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. COA of Formula: C7H13BrO2

General procedure: Benzenesulfonamide (1.2mmol), ethyl alpha-bromophenylacetate or ethyl pheny-lacetate (2.4mmol), and toluene (4mL)werecombinedinasealedtubeequippedwith astirbar.Themixturewasstirredat50Cfor10min,TiCl4 (1.8 mmol) was added, andthereactionmixturewasheatedto115C.Afteravariableperiodoftimethe mixturewasdilutedwithH2O (10mL)toremovetheexcessofTiCl4, filtered,andextracted withAcOEt(3×15mL). The combined organic layers were dried over anhydrous Na2SO4 and thesolventwasevaporatedinvacuo.Crudecompoundswere purified by flash column chromatography (silicagel;cyclohexane=AcOEt 8:2). 2-Bromo-3-methyl-N-[(4-methylphenyl)sulfonyl]butanamide (4b). Orange oil, 57% yield; IR(KBr) 3528, 3235, 2970, 2880, 1718, 1597, 1450, 1171, 1085, 865, 550 cm-1; 1H NMR (CDCl3) d0.94 (d, 3H, J 6.6 Hz, CH3), 0.96 (d, 3H, J 6.6 Hz, CH3), 2.21 (octuplet, 1H, CH3CHCH3), 2.44 (s,3H, CH3Ph), 4.08 (d, 1H, J 6.0 Hz, CHBr), 7.34 (d, 2H, J 8.1 Hz, CH Ar), 7.91 (d, 2H, J 8.1 Hz,CH Ar), 9.01 (broad s, 1H, NH); 13C NMR (CDCl3) d 20.0 and 20.3 (CH3), 21.7 (CH3Ph), 32.4(CH3CHCH3), 58.1 (CHBr), 128.5 and 129.6 (CH Ar), 134.7 (CS Ar), 145.5 (CCH3 Ar), 166.1(CONH); Anal calcd for C12H16BrNO3S: C 43.12; H 4.83; N 4.19; found C 42.99; H 4.81; N 4.18%.

The synthetic route of Ethyl 2-bromo-3-methylbutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ammazzalorso, Alessandra; Tricca, Maria Luisa; Bruno, Isabella; De Filippis, Barbara; Di Matteo, Mauro; Fantacuzzi, Marialuigia; Giampietro, Letizia; Maccallini, Cristina; Mollica, Adriano; Amoroso, Rosa; Synthetic Communications; vol. 45; 22; (2015); p. 2546 – 2554;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: trans-Ethyl 4-hydroxycyclohexanecarboxylate

4-Toluenesulfonyl chloride (18.29 g, 96 mmol) was added in several portions to a solution of ethyl 4-hydroxycyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (29.5 g, 90 mmol) in pyridine (100 mL) in an ice-water bath, and the mixture stirred, allowing to warm to RT. After the solid had dissolved, the mixture was allowed to stand. After 24 h, the mixture was concentrated and the residue partitioned between water and EtOAc (100 mL each). The organic phase was dried and concentrated to give ethyl 4-(tosyloxy)cyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (crude, 29.5 g) as a colourless oil which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta ppm 1.20-1.30 (m, 3H) 1.44-2.08 (m, 8H) 2.21-2.43 (m, 1H) 2.48 (s, 3H) 4.08-4.20 (m, 2H) 4.40-4.50 and 4.70-4.78 (both m, total 1H) 7.28-7.40 (m, 2H) 7.78-7.86 (m, 2H)

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; US2015/57298; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 51329-15-8, These common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, 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.

Methyl 3,5-dibromobenzoate (294 mg, 1.0 mmol), 6-methoxy-1,2,3,4-tetrahydroquinoline (179 mg,1.1 mmol), BINAP (31 mg, 0.05 mmol) and palladium acetate (10 mg, 0.05 mmol) were added to 8 ml of toluene, Cs2CO3 (456 mg, 1.4 mmol) was added under nitrogen gas, heated to 100C and reacted for 12 h. A small amount of ethyl acetate was added, insoluble substance was removed by filtration, and the crude product was separated with silica gel column chromatography to obtain Compound 26, which was yellow oil, 255 mg, yield 77%. 1H NMR (CDCl3): delta ppm 1.96 (2H, m, 3′-CH2), 2.76 (2H, t, J = 6.4 Hz, 4′-CH2), 3.61 (2H, t, J = 6.0 Hz, 2′-CH2), 3.78 (3H, s, OCH3), 3.89 (3H, s, OCH3), 6.65 (1H, dd, J = 8.8 Hz and 3.2 Hz, ArH-7′), 6.68 (1 H, d, J = 2.8 Hz, ArH-5′), 6.95 (1 H, d, J = 9.2 Hz, ArH-8′), 7.43 (1 H, t, J = 2.0 Hz, ArH-4), 7.66 (1 H, t, J = 2.0 Hz and 1.6 Hz, ArH-6), 7.66 (1 H, dd, J = 1.2 Hz and 0.8 Hz, ArH-2). MS m/z (%) 376 (M+H+, 100), 378 (M+3+, 91).

Statistics shows that Methyl 3,5-dibromobenzoate is playing an increasingly important role. we look forward to future research findings about 51329-15-8.

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Militaty Medical Sciences P.L.A.; XIE, Lan; WANG, Xiaofeng; LEE, Kuo-Hsiung; EP2857393; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1236357-65-5,Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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 mixture of 2-aminopyrimidine-5-boronic acid pinacol ester (221 mg, 1.0 mmol), I- 36 (200 mg, 0.74 mmol), Pd-FibreCat-1007 (75 mg, 0.045 mmol) in THF (2.0 mL) at room temperature is added 2M Na2C03 solution (0.75 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give 1-37 (75 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, category: esters-buliding-blocks

The resulting product (2.02g, 0.013mol) from step 4, ethyl 4,4,4-trifluorocrotonate (4.30g, 0.026mol) and anhydrous potassium carbonate (1.76g, 0.013mol) were dissolved in DMF (70mL), and then the system was stirred for 6hrs at 80C. At the end of reaction, the reaction system was cooled to room temperature, added with water and then extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.35g of the product (60.1 %) by column chromatography. 1HNMR(400MHz, d6-DMSO), deltappm 7.84(s,1H), 7.13(s,1H), 7.09(s,1H), 5.94(m,1H), 4.25(dd,1 H), 1.27(t,3H)

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; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, A new synthetic method of this compound is introduced below., Recommanded Product: 383-62-0

A mixture of A (5.0 g, 32.9 mmol) and ethyl 2-chloro-2,2-difluoroacetate (5.7 g, 36.0 mmol), potassium carbonate (4.5 g. 32.9 mmol) in dry DMF (90 mL) were stirred at 600C for 6 hours under an N2 atmosphere. Then the reaction was stirred at rt. for another 60 hours. Ether (200 mL) was added to the mixture and the layers separated. The organic phase was washed with water (100 mL* 3), dried over Na2SO^, evaporated and purified on silica chromatography with eluent (EtOAc: PE = 1: 12) to afford B 2.3 g.

The synthetic route of 383-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CVI PHARMACEUTICALS LIMITED; LIU, Haiyan; LI, Gaoping; WANG, Junbo; LIU, Jingwen; WO2010/75469; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 40876-98-0, The chemical industry reduces the impact on the environment during synthesis 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of0.01 mol of diethyl oxalylacetate sodium salt, 0.01 molof aromatic aldehyde, and 0.01 mol of urea was heatedat reflux in 10 mL of acetic acid for 2 h. The mixturewas kept for 24 h at room temperature, the precipitatewas filtered off and recrystallized from ethanol.

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, Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gein; Zamaraeva; Volkova; Dmitriev; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 730 – 733; Zh. Org. Khim.; vol. 52; 5; (2016); p. 740 – 743,4;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 23680-40-2, name is Methyl 3-bromopropiolate, 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 23680-40-2, SDS of cas: 23680-40-2

The product of Step A (1 1.3g, 69mmol) and f-butyl pyrrole- 1 -carboxylate (30 mL, 1 SOmmol) was combined and heated at 95 and allowed to stir at this temperature for 24 hours. The product was purified using chromatography on silica to provide compound 7OC as a yellow oil.

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

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61367-07-5, A common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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 suspension of 6-chloro-8-(cyclopropylamino)-N-(3-fluoropyridin-4- yl)imidazo[l,2-b]pyridazine-3-carboxamide (0.030 g, 0.087 mmol) and DIEA (0.227 mL, 1.298 mmol) in NMP (1 mL) was added trans-methyl 4- aminocyclohexanecarboxylate, HCl (0.201 g, 1.038 mmol). The resulting suspension was heated to 120 0C in a 300W CEM Discover microwave for 60 min. The crude material was diluted with 1 mL MeOH and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100%B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 240 min, hold at 100% B 40 min, flow rate 25 mL/min. Material was redissolved in DMSO/THF and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 60 min, flow rate 25 mL/min, to afford methyl trans-4-((8-(cyclopropylamino)-3-((3-fluoro-4- pyridinyl)carbamoyl)imidazo[l,2-b]pyridazin-6-yl)amino)cyclohexanecarboxylate, 2TFA (0.006 g, 9.97% yield) obtained as a white foam. LC/MS, m/z 468.0 (M+l). HPLC Rt = 4.120 min. YMC S5 ODS-A column (4.6 x 50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.2% H3PO4). Solvent A: (10% MeOH, 90% H2O, 0.2% H3PO4). Gradient, start % B = O, final % B = 100, gradient time 4 min, hold at 100% 1 min, flow rate 4 mL/min. 1H NMR (500 MHz, DMSO-d6) delta ppm11.46 (1 H, s), 8.67 (1 H, d, J=2.75 Hz), 8.55 (1 H, t, J=5.91 Hz), 8.41 (1 H, d, J=5.77 Hz), 8.00 (1 H, s), 7.57 (1 H, s), 7.00 (1 H, s), 6.07 (1 H, s), 2.06 (3 H, s), 1.91 (4 H, s), 1.58 (1 H, d), 1.30 (4 H, d, J=10.45 Hz), 1.05 (2 H, d, J=I 1.27 Hz), 0.76 (2 H, d, J=4.95 Hz), 0.57 – 0.67 (2 H, m).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100375; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics