Esters-buliding-blocks

Reference of 18583-89-6, A common heterocyclic compound, 18583-89-6, name is Methyl 3-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

When the same reaction as in Referential Example 18 is carried out using methyl 3-amino-2-methylbenzoate instead of the starting methyl 3-amino-6-methylbenzoate, 2-methyl-3-(1-pyrrolyl)benzyl alcohol is obtained.

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; Banyu Pharmaceutical Co., Ltd.; US5234946; (1993); A;,
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Some common heterocyclic compound, 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, molecular formula is C9H9BrO3, 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 Methyl 4-bromo-2-methoxybenzoate

Step 1: Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoateTo a 100 mL round-bottomed flask equipped with a stir bar was added methyl 4- bromo-2-methoxybenzoate (1.79 g, 7.30 mmol), 4,4,4?,4?,5 ,5 ,5?,5?-octamethyl-2,2?- bi(1,3,2-dioxaborolane) (2.78 g, 10.9 mmol), PdCl2(dppf) (0.267 g, 0.365 mmol), and potassium acetate (2.15 g, 21.9 mmol) at ambient temperature. The flask was sealed witha septum, dioxane (36.5 ml) was added, and the atmosphere was purged with N2 (g). The reaction was then heated to 90 C with stirring for 3 h and cooled to room temperature. The reaction was concentrated, the residue was dissolved in EtOAc and washed with 1 M aq. HC1 and sat. aq. NaC1. The organics were dried (Na2504), filtered, and concentrated. The residue was purified by silica gel column chromatography (Teledyne ISCOCombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep 5i02 80 g, loaded as DCM solution) to afford (methyl 2- methoxy-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoate (1 .87 g, 88 %) as a tan solid: ?H NMR (400 MHz, CDC13) oe 7.76 (d, J=7.7 Hz, 1 H), 7.42 (dd, J=7.7, 0.9 Hz, 1 H), 7.39 (s, 1 H), 3.96 (s, 3 H), 3.90 (s, 3 H), 1.36 (s, 12 H); HPLC: RT=1.284 mm(Waters Acquity BEH C,8 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1% TFA, 1.5 mill gradient, wavelength=254 nm); MS (ES): mlz= 293 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139102-34-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); 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. 623-53-0, name is Ethyl methyl carbonate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl methyl carbonate

47 mmol of the above intermediate I, 3-trifluoromethyl-4-chloroaniline 47 mmol and 0.4 mmol of benzyltrimethylammonium hydroxide weredissolved in 100 mL of N-methylpyrrolidone, and ethyl methyl carbonate 50 mmol was added dropwise in portions. The temperature was raised to 50 C for 80 min, cooled to room temperature, and the reaction solution was added to a mixed solvent of 60 mL of water and 40 mL of ethyl acetate, stirred, layered, and the aqueous phase was extracted with ethyl acetate. The sodium chloride was washed, dried, and dried under vacuum at 40 C to obtain 20.99 g of crude sorafenib in a yield of 96.1%.

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; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Hou Junkai; Liu Qingli; Tian Song; (13 pag.)CN108276327; (2018); A;,
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69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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. Recommanded Product: Methyl 4-chlorosulfonylbenzoate

Step J1 -2: methyl 6-(benzyloxy)-N-{ [4-(methoxycarbonyl)phenyl]sulfonyl}-L-norleucinate. To a solution of methyl 6-(ben2yloxy)-L-norleucinate hydrochloride (15 g, 52.1 mmol) in DCM (261 mL) was added triethylamine (15.98 mL, 115 mmol) followed by 4- carbomethoxy-phenylsulfonyl chloride (12.48 g, 53.2 mmol) by portions. After 15 minutes of stirring at room temperature, the reaction mixture was concentrated in vacuo to 1/3 volume, diluted with EtOAc, washed with 10% KHSO4, saturated aqueous NaHCtheta3, and then brine, and then dried over sodium sulfate and concentrated in vacuo to give the desired product as a crude solid. MS M+l = 450.

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/42093; (2009); A1;,
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Application of 7459-46-3,Some common heterocyclic compound, 7459-46-3, name is Triethyl ethane-1,1,2-tricarboxylate, molecular formula is C11H18O6, 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 reflux solution of triethyl 1,1,2-ethane tricarboxylate (32) (5.0 g, 20.3 mmol) and sodium borohydride (2.3 g, 60.9 mmol) in tert-butyl alcohol (40 mL), methanol (2.5 mL) was added in the reaction mixture in three aliquots over 0.5 h. The resulting solution was heated under reflux condition for additional 0.5 h and allowed to cool down to room temperature. 1 N HCl was added with care until the solution was neutral. The solution was filtered and filtrate was extracted with ethanol. The residue was purified by silica gel column chromatography (chloroform:methanol = 7:1) to give 33 (2.1 g). Yield: 88percent; 1H NMR (300 MHz, CDCl3) delta (ppm) 3.80 (m, 6H), 1.93 (q, J = 5.4 Hz, 1H), 1.71 (m, 2H); ESI [M + H] = 121.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Triethyl ethane-1,1,2-tricarboxylate, its application will become more common.

Reference:
Article; You, Hyun; Youn, Hyung-Seop; Im, Isak; Bae, Man-Ho; Lee, Sang-Kook; Ko, Hyojin; Eom, Soo Hyun; Kim, Yong-Chul; European Journal of Medicinal Chemistry; vol. 46; 4; (2011); p. 1153 – 1164;,
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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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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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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;,
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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;,
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