Month: March 2021

Some common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, 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 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

A mixture of sulfone 5 (1.58g, 7.5mmol) and 15(558 mg, 3 mmol) in freshly distilled DMF (9 mL) was added to a mixture of HgCl2 (49mg, 0.18 mmol)and Mg (183mg, 7.5 mmol) in DMF (3 mL) at ambient temperature. The reaction was heated to 75 Cand stirred for an additional 3 h. The reaction was cooled to rt and quenched with 7M HCl. The reactionmixture was then heated to 110 C and stirred for an hour. The reaction mixture was cooled to rt andextracted with diethyl ether (3), dried over MgSO4 and concentrated under reduced pressure and dried toobtain crude carboxylic acid. The crude acid was dissolved in dry DMF and added to a round-bottomedflask containing anhydrous K2CO3 (830 mg, 6 mmol) after which benzyl bromide (0.7 mL, 6 mmol) wasadded. The mixture was stirred for 2 h and then diluted with water and extracted with diethyl ether (3),washed with brine and dried over MgSO4. The ethereal layer was concentrated under reduced pressure toobtain the crude ester

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15568-85-1, its application will become more common.

Reference:
Article; Sakavuyi, Kaumba; Petersen, Kimberly S.; Tetrahedron Letters; vol. 54; 45; (2013); p. 6129 – 6132;,
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35179-98-7, name is Chloromethyl ethyl carbonate, 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. SDS of cas: 35179-98-7

To a solution of (2R,4R)-4-(t-butoxyoxalylamino)-5-(3?-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid (100 mg, 220 mumol) and chloromethyl ethyl carbonate (61 mg, 440 mol) in DMF (3 mL) was added 2,6-lutidine (72 mg, 660 mumol) and NaI (33 mg, 220 mumol). After stirring at room temperature for 24 hours, the mixture was diluted with water (20 mL) and extracted with EtOAc (2¡Á20 mL). The combined organic layers were washed with saturated aqueous NaCl (2¡Á70 mL), dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product which was further purified by preparative TLC (PE:EtOAc=2:1) to yield Compound 1 (40 mg) as a yellow solid. LC-MS: 572[M+Na]+.

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUGHES, Adam D.; FENSTER, Erik; FLEURY, Melissa; GENDRON, Roland; US2013/109639; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, 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 1000342-11-9, Recommanded Product: Methyl 3-amino-5-bromo-2-methylbenzoate

Step 1: Synthesis of tert-butyl 4-((5-bromo-3-(methoxycarbonyl)-2-methylphenyl)amino)piperidine-1-carboxylate To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (4.5 g, 18.44 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (11.01 g, 55.33 mmol) in dichloroethane (50 mL), acetic acid (6.64 g, 110.6 mmol) was added and reaction stirred at room temperature for 10 min. Then sodium triacetoxyborohydride (11.72 g, 55.28 mmol) was added at 0 C. and reaction stirred overnight at room temperature. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired compound (5.2 g, 66.24%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2876-78-0,Some common heterocyclic compound, 2876-78-0, name is Methyl 1-Naphthaleneacetate, molecular formula is C13H12O2, 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.

Step 1 potassium 1-(methoxycarbonylmethyl)-4-naphthalene sulfonate A solution of methyl 1-naphthaleneacetate (1 mL, 5.77 mmol) in carbon tetrachloride (1 mL) was cooled under nitrogen in an ice bath. Chlorosulfonic acid (0.38 mL, 5.7 mmol) was added dropwise over 8 minutes. After an additional 30 minutes, the viscous mixture was removed from the bath and was stirred at room temperature for 17 hours to give a white solid. The solid was partitioned between methylene chloride (5 mL) and water (5 mL). After filtering through solka-floc, the methylene chloride layer was extracted with more water (2*5 mL), and the combined aqueous extracts were basified with potassium carbonate to give a precipitate. The suspension was concentrated to approximately 5 mL and was cooled in an ice bath. The suspension was then filtered and the collected solid was washed with cold water (2 mL). The solid was dried under a stream of nitrogen to give the title compound as a white solid (0.84 g). 1H NMR (DMSO-d6, 500 MHz) delta 3.73 (s, OMe), 4.27 (s, CH2Ar), 7.53 (d, ArH), 7.71 (t, ArH), 7.76 (t, ArH), 8.06 (d, ArH), 8.10 (d, ArH) and 8.73 (d, ArH).

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-Naphthaleneacetate, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6271222; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 35180-01-9, A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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.

EXAMPLE 1Process for the Preparation of Tenofovir Disoproxil FumarateToluene (500 ml) was added to the Tenofovir (100 gm) and stirred at room temperature. To this triethylamine (66.31 gm) was added, temperature was raised to 90 C. and water was collected by azeotropic distillation at 110 C. Toluene was completely distilled under vacuum at same temperature. The reaction mixture was cooled to room temperature and to this a mixture of N-methyl pyrrolidine (300 gm), triethylamine (66.31 gm), Tetrabutyl ammonium bromide (52.8 gm) and trimethyl silyl chloride (17.8 gm) were added. The above reaction mixture was heated to 50-55 C. and was added slowly chloromethyl isopropyl carbonate (CMIC) and maintained the reaction mixture at 50-55 C. for 5 hrs. (Qualitative HPLC analysis shows about 85% product formation). The above reaction mixture was cooled to room temperature and filtered. The filtrate was added to DM water at 5-10 C. and extract with dichloromethane. The combined dichloromethane layer was concentrated under vacuum and the crude was Co-distilled with cyclohexane and this crude was taken into isopropyl alcohol (1000 ml). To this fumaric acid (38 gm) was added and temperature was raised to 50 C. The reaction mixture was filtered and filtrate was cooled to 5-10 C. The obtained solid was filtered and washed with isopropyl alcohol. The compound was dried under vacuum to yield Tenofovir Disoproxil fumarate (140 gm).

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Datta, Debashish; Vellanki, Siva Rama Prasad; Sahu, Arabinda; Balusu, Raja Babu; Ravi, Mastan Rao; Nandipati, Hari Babu; Rama, Shankar; Vadali, Lakshmana Rao; Gorantla, Srikanth Sarat Chandra; Dasari, Srinivasa Rao; Mittapelly, Nagaraju; US2013/5969; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-24-9, name is Ethyl 4-chlorophenylacetate, 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. category: esters-buliding-blocks

A solution of (4-chlorophenyl) acetic acid (20.0 g, 0.12 mol) and conc sulfuric acid (2 g) in [ETOH] (150 mL) was heated under reflux for 19 h, cooled, and then concentrated. Diethyl ether (100 mL) was added and the solution was washed with sat’d NaHCO3 solution (40 mL x 2), dried, and the volatiles removed. This provided (4- chlorophenyl) acetic acid ethyl ester as an oil (22.3 g, 96%). Ethyl formate (7.46 g, 0. [101 MOL)] was added dropwise to a stirred ice-cooled suspension of (4-chlorophenyl) acetic acid ethyl ester (20.0 g, 0. [101] mol) and NaH (0.131 mol) in diethyl ether (100 mL). The mixture was then allowed to warm to room temperature overnight. The mixture neutralised (1 M HC1) ; the organic layer was isolated, dried, and the solvent removed to give [2- (4-CHLOROPHENYL)-3-OXO-PROPANOIC] acid ethyl ester as a colourless solid (19.8 g, [87%). 1H NMR (CDCL3)] : [No. ] 12.14 (d, J=12. 8,1 H), 7. [31-7.] 18 (m, 4 H), 4.29 (q, [J=7.] 2,2 H), 1.57 (br, [1] H), 1.29 (t, J=7, 2,3 H).

The synthetic route of 14062-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Prana Biotechnology Limited; WO2004/31161; (2004); 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 52727-57-8

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0 C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-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; Universitat des Saarlandes; US2011/112067; (2011); 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. 37722-82-0, name is Methyl 3-Hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Formula: C8H14O3

Methyl 3-oxocvclohexanecarboxylateRuthenium (IV) oxide hydrate (1.47 g, 1 1.1 mmol) and sodium bromate (100 g, 664 mmol) were combined in diethyl ether (600 mL) and water (300 mL). The resulting black mixture was stirred for 10 min and then cooled in an ice bath. Methyl 3- hydroxycyclohexanecarboxylate (35 g, 221 mmol) was dissolved in ether (to bring total volume to 100 mL) and was added dropwise to the ice cold reaction mixture. The temperature was not allowed to go above 30 C. The reaction mixture was stirred for 1 h with the reaction temperature at -15 C. Isopropanol was carefully added to the reaction mixture at a rate necessary to keep the reaction temperature at -27 C. The layers were separated and the organic layers were washed with ether. The combined organics were washed with saturated aqueous NaHC03 solution and brine. The organics were then dried over MgS04, filtered, and concentrated to provide methyl 3-oxocyclohexanecarboxylate (34.5 g, 100 % yield) which was used without further purification. H NMR (400 MHz, CDCI3) delta 3.68 (s, 3H), 2.79 (m, 1 H), 2.52 (d, J = 7.78 Hz, 2H), 2.23 – 2.42 (m, 2H), 1.98 – 2.15 (m, 2H), 1.82 (d, J = 10.29 Hz, 1 H), 1.61 – 1.77 (m, 1 H).

The synthetic route of 37722-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, 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 383-62-0, COA of Formula: C4H5ClF2O2

EXAMPLE 174(R)-5-(5-(Difluoromethoxy)pyrimidin-2-yloxy)-N-(4-(morpholin-2-yl)phenyl)pyrimidin-2-aminea) 2-Chloro-5-(5-(difluoromethoxy)pyrimidin-2-yloxy)pyrimidine2-Chloropyrimidin-5-ol (0.5 g) was combined with DMF (5 ml) to give a colourless solution. K2CO3 (582 mg) and ethyl 2-chloro-2,2-difluoroacetate (534 mul) were then added. The reaction mixture was stirred at 70 C. overnight to afford a brown suspension. The reaction mixture was then poured into EtOAc and washed sequentially with water and with saturated brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel; gradient: 0% to 60% EtOAc in hexanes) to afford 2-chloro-5-(5-(difluoromethoxy)pyrimidin-2-yloxy)pyrimidine (154 mg, 15%) as a yellow solid. MS (ISP): 277.0 ([{37Cl}M+H]+), 275.0 ([{35Cl}M+H]+).

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; Galley, Guido; Norcross, Roger; Pflieger, Philippe; US2012/245172; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, 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.

Step B: Methyl 3-amino-2-fluorobenzoate; In a 500 mL flask was placed 1,1-dimethylethyl carbamate (6.03 g, 51.5 mmol), methyl 3-bromo-2-fluorobenzoate (10 g, 42.9 mmol), Pd2(dba)3.CHCl3 (0.89 g, 0.86 mmol), xantphos (1.49 g, 2.57 mmol) and cesium carbonate (16.8 g, 51.5 mmol). The flask was sealed with a rubber septum, placed under high vacuum, and toluene (200 mL) was added. Three cycles of high vacuum/N2 were performed and the reaction mixture was stirred at 90 C. overnight. The reaction was filtered through a pad of celite with EtOAc washing and concentrated. To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h. The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over NaSO4, stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc:Hexane to give 5.53 g (76%) of the title compound of Step B. 1H-NMR (400 MHz, DMSO-d6) delta 6.92-7.01 (m, 3H), 5.37 (s, 2H), and 3.81 (s, 3H). MS (ESI): 170 [M+H]+.

The synthetic route of 206551-41-9 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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics