Tag: M.W=100-200

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;,
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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;,
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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;,
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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;,
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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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Synthetic Route of 73368-41-9, 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. 73368-41-9, name is Ethyl 4-amino-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)-ethyl 4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2- yl)amino)-3-methoxybenzoate (i?)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (88.4 mg, 0.30 mmol, 1 eq), ethyl 4-amino-3-methoxybenzoate (70.3 mg, 0.36 mmol, 1.2 eq), Pd2dba3 (13.7 mg, 0.015 mmol, 5 mol%), XPhos (21.5 mg, 0.045 mmol, 15 mol%) and K2C03 (166 mg, 1.2 mmol, 4 eq) were dissolved in tBuOH (3 mL, 0.1 M) and heated to 100 C for 20 hours. The mixture was filtered through celite, washed with DCM and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-100% EtOAc/hexanes, 12 minute gradient) gave the desired product as a dark yellow oil (119 mg, 0.262 mmol, 87%). 1H NMR (400 MHz, Chloroform-;/) delta 8.57 (d, J= 8.5 Hz, 1H), 7.68 (tt, J = 4.2, 2.1 Hz, 3H), 7.53 (d, J= 1.4 Hz, 1H), 4.50 (q, J= 7.4 Hz, 1H), 4.36 (qd, J= 7.1, 1.2 Hz, 2H), 4.22 (dd, J= 7.8, 3.6 Hz, 1H), 3.96 (d, J= 1.2 Hz, 3H), 3.32 (d, J= 1.3 Hz, 3H), 2.22 – 2.10 (m, 1H), 2.04 – 1.96 (m, 1H), 1.89 – 1.78 (m, 4H), 1.70 (dq, J= 14.2, 8.2, 7.4 Hz, 4H), 1.39 (td, J= 7.1, 1.2 Hz, 3H), 0.91 – 0.82 (m, 3H). LCMS 453.80 (M+H).

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

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
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Electric Literature of 454-31-9, These common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 2: Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US6407140; (2002); B1;,
Ester – Wikipedia,
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Application of 927-68-4, These common heterocyclic compound, 927-68-4, name is 2-Bromoethyl 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.

A solution of Intermediate 11 (470 mg, 1.50 mmol), 2-bromoethyl acetate (1.00 g, 5.99 mmol) and DBU (913 mg, 6.01 mmol) in DMF (3 ml) was heated under argon at 80QC for 1.5 h. On cooling the reaction mixture was diluted with EtOAc (50 ml) and 1M aqueous HCI (50 ml). The organic layer was separated, washed with water (40 ml) and brine (40 ml), dried (Na2SO4) and evaporated. The crude product was chromatographed on an Isolute Si Il cartridge (20 g) eluting with 50-100% EtOAc in pentane.Yield: 457 mg (63%)LC-MS (Method 1): Rt 3.22 min, m/z 486 [MH+]

Statistics shows that 2-Bromoethyl acetate is playing an increasingly important role. we look forward to future research findings about 927-68-4.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2007/107706; (2007); A2;,
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Related Products of 19064-14-3, A common heterocyclic compound, 19064-14-3, name is Ethyl 2,6-difluorobenzoate, molecular formula is C9H8F2O2, 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 2: 1.5M t-BuLi in pentane (193 mL, 289 mmol) was added to a solution of the intermediate of step 1 (20.0 g, 96.1 mmol) and TMEDA (43.5 mL, 289 mmol) in dry THF (600 mL) at -70X under inert atmosphere and the RM was stirred for 1 h at -50C. A solution of ethyl 2,6-difluorobenzoate (21.5 g, 115 mmol) in dry THF (200 mL) was added at -70C and the RM was stirred for 1 h at -70C, 1 h at 0C and 2 h at rt. The RM was quenched with 5.5M HCI (600 mL) and heated at 70C for 5 h. The mixture was cooled to rt, neutralized through the addition of NaHC03 and extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure. The residue was purified by CC (silica gel, CH2CI2/MeOH) to yield the desired compound (5.5 g, 25%).

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; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (2015); A1;,
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Related Products of 94994-25-9, These common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, 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.

[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl](triphenyl)phosphonium bromide (4-A, Synthesis: 532 (1986)) (5.99 g, 12.7 mmol) was stirred in dry THF (200 mL). Potassium bis(trimethylsilyl)amide (20.4 mL, 2M soln in toluene, 10.2 mmol) was added. The reaction was allowed to stir for 30 min. The reaction mixture was then cooled to -78 C. Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate was added at -78 C. by cannula. The reaction was allowed to warm to room temperature overnight. The volume was reduced by evaporation of THF in vacuo. 100 mL of water was added. The mixture was then layered with 100 mL of diethyl ether. The ether was extracted and dried (MgSO4). The product (methyl 4-[(1E)-3-(2-methyl-1,3-dioxolan-2-yl)prop-1-enyl]bicyclo[2.2.2]octane-1-carboxylate (4-B)) was purified by flash chromatography on silica gel with 10/90 ethyl acetate-hexane mixture.

The synthetic route of 94994-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Waddell, Sherman T.; Santorelli, Gina M.; Maletic, Milana M.; Leeman, Aaron H.; Gu, Xin; Graham, Donald W.; Balkovec, James M.; Aster, Susan D.; US2004/133011; (2004); A1;,
Ester – Wikipedia,
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