Category: esters-buliding-blocks

These common heterocyclic compound, 122-72-5, name is 3-Phenylpropyl 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. HPLC of Formula: C11H14O2

General procedure: A general procedure for the manganese-catalysed benzylic amination is as follows. A Teflon stir bar and 5 A powdered molecular sieves (40 mg) were added in a 10 ml round-bottom flask, which was sealed with a Suba Seal rubber septum, placed under vacuum, flame-dried for 45 s to activate the molecular sieves, cooled under a purged and completely air-free argon balloon and wrapped in foil to exclude light. Once cooled, solvent (0.40 ml, 0.5 M to substrate) and substrate (0.20 mmol, 1 equiv.) were added and stirred for 10 min. Manganese(iii) perchlorophthalocyaninechloride 3 (23.1 mg, 0.020 mmol, 0.1 equiv.) and silver hexafluoroantimonate (6.9 mg, 0.020 mmol, 0.1 equiv.) were weighed in a foil-wrapped 1-dram vial in the glove box and sealed with a Teflon cap. The vial was removed from the glove box and the contents added directly to the round-bottom flask while maintaining an argon atmosphere, then stirred for 10 min at room temperature. In a 1-dram vial open to air, 2,2,2-trichloroethyl (phenyl-lambda 3-iodanylidene)sulfamate (172.2 mg,0.40 mmol, 2 equiv.) was weighed and added directly to the round-bottom flask while maintaining an argon atmosphere. The Suba Seal rubber septum was replaced by a polyethylene cap, sealed tightly, and placed in a 40 C oil bath for 8 h with stirring. Upon reaction completion, the reaction was filtered through a 1 inch silicagel plug using diethyl ether or ethyl acetate as the eluent. The crude material was concentrated and dry-loaded directly onto a silica gel column.

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

Reference:
Article; Clark, Joseph R.; Feng, Kaibo; Sookezian, Anasheh; White, M. Christina; Nature Chemistry; vol. 10; 6; (2018); p. 583 – 591;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C7H14ClNO3

To available thiophen-3-ylamine 2p1 (0.50 g, 5.04 rnmol) was added imidate2g2 (1.08g, 5.5mmol) in ethanol (10 mL) under a N2 atmosphere. The mixture wasstirred at R.T. for 3 h at which point the reaction was concentrated. To the residuewas added ether, and the suspension filtered and washed with ether to afford adduct2p2(1.0g, 82percent). This material was sufficiently clean to be used in the subsequentstep. MS: 242.1 (MH)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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Application of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Some common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, 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. name: Methyl 3,4-dimethoxybenzoate

Example 1 Synthesis of 3,4-dimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 8.9 gm of the target compound as colorless needles (yield: 65%). Melting Point: 52.3-53.3 C. IR(gammaKBr, cm-1): 1602, 1521, 1470, 1446, 1365, 1299, 1266, 1218, 1188, 1131, 885, 786, 729. 1 H-NMR(CDCl3, delta): 1.26(9 H, s, t-C4 H9), 3.95(3 H, s, OCH3), 3.96(3 H, s, OCH3), 6.24(1 H, s), 6.90(1 H, d, J=8.4 Hz), 7.49(1 H, s), 7.51(1 H, d, J=8.4 Hz). Elemental analysis: Calculated (%) C: 68.16, H: 7.63; Found (%) C: 68.23, H: 7.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2150-38-1, its application will become more common.

Reference:
Patent; Kao Corporation; US5146002; (1992); 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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 3-(4-aminophenyl)acrylate

The appropriate amino acid derivative from Example 9 (0.020 g, 0.05 mmol) was dissolved in DCM (1 mL). DMAP (0.018 g, 3 equivalents), Et3N (20 muL, 0.15 mmol, 3 equivalents), BroP (0.058 g, 0.15 mmol, 3 equivalent), and ethyl-4-aminocinnamate (0.029 g, 0.015 mmol, 3 equivalents) were added and the mixture stirred for 20 h at room temperature. Camphor-10-sulfonic acid (CSA; 0.046 g, 0.2 mmol, 4 equivalents) was added and the reaction mixture was stirred for an additional 24 h at room temperature.

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 5048-82-8.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2003/236251; (2003); A1;,
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Synthetic Route of 17449-48-8,Some common heterocyclic compound, 17449-48-8, name is Dimethyl 5-fluoroisophthalate, molecular formula is C10H9FO4, 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.

Concentrated [HC1] (30 ml) was added to a cooled [(-5C)] suspension of dimethyl 5-amino isophthalate (20 g, 95.6 mmol) in water (75 ml), followed by portionwise addition of [NAN02] (7.5 g, 109 mmol). The reaction mixture was then stirred for 15 min. , after which [HBF4 (18] ml, 100 mmol, 48% aqueous solution) was added. The resulting mixture was stirred at [0C] for 30 min. and the precipitate formed was collected by filtration and washed with cold methanol (60 ml) and ether (60 ml). The residue was then decomposed by heating in an oil bath [(~110C).] The cooled mixture was then diluted with ether, concentrated onto silica gel and purified by flash chromatography with 5% ethyl acetate hexane as eluant giving 9.0 g (44%) of product as a white fluffy [SOLID. LH NE (CDC13), 6] [(PPM)] : 8.57 (s, 1H), 7.95 (d, 2H), 3.97 (s, 6H). A suspension of 5-fluoro-isophthalic acid dimethyl ester (1.7 g, 8. 0 mmol) in methanol (41 ml) was treated with 1.0 N sodium hydroxide (7.2 ml, 7.2 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1.0 N [HC1] to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 1.3 g (83%) of 5-fluoro-isophthalic acid monomethyl ester was isolated as a white [SOLID. LH] NMR (DMSO), [5] (ppm): 8.31 (t, 1H), 7.96 (m, 2H), 3.91 (s, 3H). Triethylamine (2.2 ml, 16.0 mmol) and isobutyl [CHLOROFORMATE] (1.0 ml, 8. 0 mmol) were added to an ice-cooled solution [OF 5-FLUORO-ISOPHTHALIC] acid monomethyl ester (1.3 g, 6.7 mmol) in dichloromethane (20 ml) and then warmed to room temperature. After stirring for 2 h, the reaction mixture was filtered and concentrated. The residue was re-dissolved tetrahydrofuran (10 ml) and then sodium borohydride [(1.] 1 g, 29.02 mmol) in water (3ml) was added drop-wise. After 1 h, the reaction was quenched with methanol and then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Flash column chromatography on silica gel using 30% ethyl acetate in hexanes afforded 667 mg (54%) of 3-fluoro-5-hydroxymethyl-benzoic acid methyl ester as a colorless [OIL. 1H] NMR [(CDC13),] [8] (ppm): 7.82 (s, 1H), 7.63 (d, 1H), 7.32 (d, 1H), 4.76 (s, 2H), 3.93 (s, 3H). Ethanol (2 ml) was added to round bottom flask containing 3-fluoro-5-hydroxymethyl- benzoic acid methyl ester (667 mg, 3.6 mmol) and palladium (10 wt. % on activated carbon, 300 mg) under argon. The flask was evacuated using a water aspirator and then filled with hydrogen from a balloon. After stirring for 2 h, the palladium on carbon was removed by filtration through celite. The filtrate was then concentrated to afford 520 mg (87%) of 3-fluoro-5-methyl-benzoic acid methyl [ESTER. LH] NMR [(CDC13),] 8 (ppm): 7.65 (s, 1H), 7.51 (d, 1H), 7.08 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H). 0.5 N Lithium hydroxide (7.4 ml, 3.7 mmol) was added to a solution 3-fluoro-5-methyl- benzoic acid methyl ester (520 mg, 3.1 mmol) in tetrahydrofuran (7.4 ml). The reaction was stirred at [75 C] for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 10% [HC1] (aq. ). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 469 mg (98%) [OF 3-FLUORO-5-METHYL-BENZOIC] acid as a white solid. 1H NMR (DMSO), d (ppm): 7.62 (s, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 2.38 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 5-fluoroisophthalate, its application will become more common.

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 5445-17-0

To a solution of E/Z mixture (5:1) of 2-propenylphenol (2.0 g, 14.9 mmol) in anhydrous DMF (30 mL) was added K2CO3 (2.68 g, 19.37 mmol) at 0 C. After stirring for 30 min at room temperature, methyl 2-bromopropionate (2.5 mL, 22.36 mmol) was added drop-wisely to the reaction mixture with a syringe. The reaction mixture was stirred for 10 h at room temperature, and poured into water (100 mL). The organic compounds were extracted with EtOAc (3 x 50 mL). The combined organic layer was washed with brine, dried (MgSO4), and concentrated under vacuum. Purification by silica gel chromatography (EtOAc/hexane=1/9, v/v) afforded the desired product as a colorless oil (3.34 g, 96%).

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:
Article; Lee, Sujin; Shin, Ju Yeon; Lee, Sang-Gi; Tetrahedron Letters; vol. 54; 7; (2013); p. 684 – 687;,
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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. Quality Control 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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Some common heterocyclic compound, 87639-57-4, name is Dimethyl 4-bromophthalate, molecular formula is C10H9BrO4, 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: C10H9BrO4

Example 1; Compound No. 1: Synthesis of 4-phenyl ethynyl dimethyl phthalate; Under a nitrogen gas stream, 24.6 g of 4-bromo-dimethyl phthalate, 11.03 g of ethynyl benzene, 71 mg of triphenylphosphine, 20 mg of trans-dichloro-bis (triphenylphosphine)palladium (II) and 171 mg of cuprous iodide were placed in a three-necked flask of 300-ml capacity and, then, 60 ml of triethylamine was poured therein while stirring. The reaction mixture was refluxed for 12 hours while heating at 100 C., cooled to room temperature and, thereafter, the resultant reaction solution was filtered to remove formed salts and catalysts and, then, washed with 60 ml of toluene. The filtrate and a rinsing solution were combined and concentrated, to obtain 25.1 g of a crude crystal of 4-phenyl ethynyl diethyl phthalate. The thus-obtained crude crystal was recrystallized from a mixed system comprising 2-propanol/n-hexane (50 ml/100 ml), to thereby obtain 22.9 g of 4-phenyl ethynyl diethyl phthalate. The yield thereof was 86.4%. 1H-NMR (CDCl3): 3.92 ppm (s, 3H), 3.93 ppm (s, 3H), 7.36 to 7.39 ppm (m, 3H), 7.52 to 7.56 ppm (m, 2H), 7.66 ppm (q, 1H), 7.75 ppm (d, 1H), 7.85 ppm (d, 1H) IR vmax (KBr): 1269 (s), 1604 (m), 1724 (s), 2210 (w), 2950 (w), 3003 (w) cm-1 MS: m+/z=295 Melting point: 76.9 C. to 77.4 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87639-57-4, its application will become more common.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2005/215820; (2005); A1;,
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Reference of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick 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-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
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