Category: esters-buliding-blocks

Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

PREPARATION 1: 1 – Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde; Step a: 4-(/ert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester:; [00160] To a 50 mL flask was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (5.0 g; 29.0 mmol), imidazole (2.37 g; 34.8 mmol), DMF (30 mL) and ter/-buryldimethylsilyl chloride (4.81 g; 32.0 mmol). The solution was stirred for 78h at 20 0C. The reaction was diluted with EtOAc (100 mL), washed with water 2 x 100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude oil was purified by flash chromatography (silica gel, hexanes/EtOAc 1:0 to 1:1) to give pure product (7.79 g, 94% yield) as a 2:1 mixture of diastereomers.1H-NMR (400 MHz, CDCl3) (J = Hz) delta mixture 4.12 (m; 2H), 3.90 (m; 0.65H), 3.58 (m; 0.35H), 2.23 (m; IH), 1.98 (m; 3H), 1.82 (m; 3H), 1.49 (m; 2H), 1.21 (m; 3H), 0.88 (s; 9H), 0.05 (s; 3H), 0.03 (s; 3H). 13C-NMR (400 MHz, CDCl3) delta mixture 175.7, 175.6, 70.5, 66.6, 60.1, 60.0, 42.2, 42.1, 34.8, 32.8, 27.2, 25.8, 25.6, 23.4, 18.2, 18.0, 14.2, -4.7, -4.9. MS (ES+) m/z 287.22 [MH+].

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

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
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Related Products of 136333-97-6,Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

Example 11A Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl}ethyl]malonate At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. The mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid. LC-MS (Method 2): Rt=2.92 min; m/z=495 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(2-bromoethyl)benzoate, its application will become more common.

Reference:
Patent; Hahn, Michael; Becker, Eva-Maria; Knorr, Andreas; Schneider, Dirk; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Lang, Dieter; US2010/197680; (2010); A1;,
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Application of 174579-31-8, These common heterocyclic compound, 174579-31-8, name is tert-Butyl 2-(4-aminophenyl)acetate, 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.

Synthesis of compound 2.6. A solution of compound 2.5 (1.0 g, 3.19 mmol, 1.0 eq), tert-butyl 2-(4-aminophenyl)acetate (0.661g, 3.19 mmol, 1.00 eq) and K2C03 (1.32 g, 9.57 mmol, 3.0 eq) in DMF (10.0 mL) was heated at 90 C for 12 hours. Upon completion, the mixture was cooled to room temperature and poured into water. The product was extracted with ethyl acetate (50mL X 3). And the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified using flash column chromatography to afford the compound 2.6 (1.10g, 71.4%) MS (ES): m/z 484.2 [M+H]+.

The synthetic route of 174579-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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These common heterocyclic compound, 140-11-4, name is Benzyl acetate, 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. Application In Synthesis of Benzyl acetate

General procedure: Bioreactor cultures and biotransformations using E. coli JM109(pDTG601). Growth and biotransformation in the bioreactor usingE.coli JM109 (pDTG601) were carried out using a modification ofour previously published procedure.3b Thus, 5 mL of LB mediumsupplemented with ampicillin sodium salt (0.1 g/L) and glucose(5 g/L) were inoculated with a single colony of E. coli JM109(pDTG601), and grown overnight at 37 C and 150 rpm. Two500 mL shake-flasks containing 150 mL of MSB medium wereinoculated with 1 mL of the grown culture. These precultureflasks were placed in an orbital shaker at 37 C and 150 rpm, for12 hrs. Both entire cultures were used to inoculate the bioreactor(Sartorius Biostat A plus), charged with an initial volume of 2.5 L,and set to 500 rpm, 30 C, and air flow rate of 4L/min. The pHvalue was controlled automatically to 6.8 by addition of conc.ammonium hydroxide during the whole process. A pulse ofantifoam agents (Aldrich?s Antifoam Y: Silicone dispersion inwater 1:1) was added at the beginning of the run. At 6 h afterinoculation the dissolved oxygen value sharply increased(indicating carbon deprivation), whereupon a glucose fed-batchwas started by adding glucose (0.7 g/mL solution) from an initialrate of 0.08 mL/min to 0.54 mL/min in a 20 h period. When thebiomass concentration reached 15 g/L cdw, IPTG was added toinduce toluene dioxygenase expression (IPTG final concentrationin bioreactor of 10 mg/L), and the stirrer speed was set to900 rpm. After the culture reached the stationary phase (c.a.26 h, 50 g/L cdw aprox), glucose feeding was decreased to0.25 mL/min and substrate addition was started. A solution of thecorresponding substrate in liquid paraffin (0.5 M) was added at aflow rate of 20 mL/min using a peristaltic pump. After thebiotransformation was completed, the pH of the medium in thebioreactor was adjusted to 7.5. The culture broth was centrifugedat 7000 rpm and 4 C for 30 min, the supernatant was collectedand the cell pellet properly disposed. Centrifugation led to theseparation of the liquid paraffin (which contains no detectableamounts products) from the aqueous phase. The latter wasproperly lyophilized overnight to obtain a dry powder, whichwas extracted several times with ethyl acetate until no morediols were detected by TLC. The solvent was evaporated to affordthe corresponding diol, which was washed several times withhexanes to remove the liquid paraffin traces.

The synthetic route of Benzyl acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pazos, Mariana; Martinez, Sebastian; Vila, Maria Agustina; Rodriguez, Paola; Veiga, Nicolas; Seoane, Gustavo; Carrera, Ignacio; Tetrahedron Asymmetry; vol. 26; 24; (2015); p. 1436 – 1447;,
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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 541-16-2 as follows. Recommanded Product: 541-16-2

Compound 185a (3.15 g, 8.39 mmol) was dissolved in 50 mL of tetrahydrofuran,3.81 mL of tert-butoxycarboxylic anhydride (i.e., di-tert-butyl dicarbonate Boc2O, 16.78 mmol) and 100 mg of p-dimethylaminopyridine,Room temperature reaction 4h.The residue was purified by column chromatography, eluting with petroleum ether: ethyl acetate = 20: 1 (v / v) to give 3.18 g of compound 185b in 91% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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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. 2216-92-4, name is N-Phenylglycine Ethyl Ester, This compound has unique chemical properties. The synthetic route is as follows., Safety of N-Phenylglycine Ethyl Ester

Example 71 Synthesis of 3-(2-naphthylsulfonyl)-1-(phenyl)-imidazolidin-2,4-dione (Compound 71): In a similar manner to Example 70, 470 mg (1.28 mmol; yield: 26.6%) of the title compound were obtained as white crystals from 860 mg (4.83 mmol) of ethyl N-phenylamino-acetate and 1.39 g (81%, 4.83 mmol) of 2-naphthalenesulfonyl isocyanate. Melting point: 208-210 C. PMR (delta ppm, DMSO-d6): 4.52(s,2H), 7.1-8.3(m,11H), 8.76(s,1H).

According to the analysis of related databases, 2216-92-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suntory Limited; US5691335; (1997); A;,
Ester – Wikipedia,
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Related Products of 685892-23-3, 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4; 4′-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester Step A: 4′-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester A mixture of {(R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), methyl 2-bromo-6-chlorobenzoate (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 mumol), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 mumol) in THF (20.0 ml) and water (1.18 ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM/EtOAc 100:0-90:10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]-.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-6-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
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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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H13BrO2

Preparation of Intermediate 1 -bromo-4-(1 -methoxy-2-methylpropan-2-yl)benzene (1AA- 11; Methyl 2-(4-bromophenyl)-2-methylpropanoate (23.5g, 86.6mmol) in tetrahydrofuran (175ml_) was cooled to -78C. Lithium aluminum hydride (100 ml. of 1.0 M solution) added slowly over 45 minutes and stirred for 3 hours at cold temperature. Reaction solution was slowly diluted with ethyl acetate and stirred for 10 minutes. 1 M hydrochloric acid was slowly added drop wise to reaction mixture. Diethyl ether (20OmL) added and layers separated. Organic washed with 1 M hydrochloric acid, brine, dried over sodium sulfate, filtered and concentrated to give 2-(4-bromophenyl)-2- methylpropan-1-ol (20m, 100%) as a white solid.

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; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
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23877-12-5, Adding some certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5.

2-Methyl-2-{4-[3-(4-trifluoromethyl-phenyl)-[1,2,4]thiadiazol-5-ylmethylsulfanyl]-phenoxy}-propionic acid tert-butyl ester To a three-necked flask containing NaH (36 mg, 0.90 mmol; 60% in mineral oil) was added a solution of B1 (220 mg, 0.598 mmol) in THF. To the mixture at 40 C. was added tert-butyl 2-bromoisobutyrate (287 mg, 1.29 mmol). After heating at 70 C. for 2 h, more tert-butyl 2-bromoisobutyrate (215 mg, 0.970 mmol) was added and the heating was continued overnight. The mixture was quenched with water (0.1 mL), concentrated, and chromatographed (EtOAc/hexane) to give 81 mg (27%) of B2; 1H NMR (300 MHz, CDCl3) delta 8.35 (d, J=8.2 Hz, 2 H), 7.71 (d, J=8.2 Hz, 2 H), 7.34 (d, J=8.8 Hz, 2 H), 6.78 (d, J=8.7 Hz, 2 H), 4.42 (s, 2 H), 1.55 (s, 6 H), 1.38 (s, 9 H); MS (ES) m/z: 511 (M+H+).

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 23877-12-5.

Reference:
Patent; Kuo, Gee-Hong; Shen, Lan; Wang, Aihua; Zhang, Yan; US2005/96362; (2005); A1;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 5-amino-2-fluorobenzoate

A solution of 5-amino-2-fluorobenzoic acid methyl ester (340 mg, 2 mmol), 6-mercaptonicotinic acid (310 mg,2 mmol), and EEDQ (500 mg, 2 mmol) in anhydrous DMF (4 mL) was stirred overnight under N2 at room temperature,2-Bromomethylphenyl boronic acid (428 mg, 2 mmol) was added to the reaction mixture for another 16 hours at roomtemperature. The solvent was then removed by rotary evaporation, and the residue dissolved in EtOAc (25 mL), Theorganic layer was washed with H2O, 10% Na2CO3, H2O, 1 N HCl, H2O, brine, and dried over Na2SO4. The organic layerwas filtered and evaporated to yield 597 mg (68%) of the methyl ester derivative as a light yellow solid. The methyl esterintermediate (200 mg, 0.45 mmol) was dissolved in MeOH (6 mL) and 1 N NaOH (1.35 mL) was added to the reactionmixture. The reaction was stirred for 16 hours at room temperature. The MeOH was removed by rotary evaporation,and the resulting solution acidified with IN BCl. The resulting solid was washed and dried to yield 87 mg (45%) as anoff white solid. ESI-MS m/z = 426.93 [M+H]+

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; Syntrix Biosystems, Inc.; Maeda, Dean Y.; Zebala, John A.; EP2942346; (2015); A1;,
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