Category: esters-buliding-blocks

581065-95-4, These common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 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.

In the glove box under an atmosphere of dry nitrogen, a 3000 mL, 4-necked flask was charged with bis-CBZ-Lysine (200.0 g, 483 mmol), EDC (139 g, 724 mmol), and 1500 mL of 2:1 tetrahydrofuran:tert-butyl methyl ether. The flask was fitted with an immersion well; the remaining joints were stoppered, and the flask was transferred to the fume hood where one of the stoppers was replaced with an addition funnel connected by a gas inlet adapter to a bleed of dry nitrogen. The flask was placed in a salted ice-water bath, fitted with an overhead stirring apparatus, and stirred until 0[deg.] C. was attained. In the glove box under a dry nitrogen atmosphere, amino-dPEG(R)4-TBE (163 g, 507 mmol) was dissolved in tetrahydrofuran (170 ml). The PN10221 was then poured into the addition funnel under a nitrogen shower and added slowly by drop, keeping the temperature as close to [deg.] C. as possible. The reaction was allowed to continue overnight, warming slowly to ambient. The reaction appeared complete the next morning by TLC and RP-HPLC. Stirring of the reaction mixture was stopped, and the EDU was allowed to settle for several hours. The solution was then decanted from the EDU goo. The reaction solvent was removed by rotary evaporation under reduced pressure at 45[deg.] C. The residue was then dissolved in dichloromethane to a final volume of 1400 mL and washed once with 250 mL with 10% aqueous HCl, then once with 400 mL of 5% brine. The DCM was removed by rotary evaporation at 35[deg.] C., and the residue was dried by rotary evaporation at 45[deg.] C. under high vacuum for about 1 hour. Yield: 330 gms (95.4%) HPLC (AMINES3045FF METHOD): 96.2% purity by ELSD. TLC: Ethyl Acetate:Methanol 8:2. Major spot at Rf=0.69 with both UV quench at 254 nm and iodine-positive reaction. One minor UV quenching spot (no iodine reaction) near solvent front. No ninhydrin-positive spot. NMR: (400 MHz, CDCl3, [delta]): 7.322 (m, 11H, 2 CBZ rings & NH); 6.737 (s, 1H, amide); 5.762 (s, 1H, amide); 5.084 (m, 4H, 2*CH2O from CBZ); 4.153 (q, 1H, CHN on lysine); 3.526 (t, 2H, CH2 to N on lysine sidechain); 3.425 (t, 2H, CH2 [beta] to N on dPEG(R)); 3.164 (t, 2H, CH2N on PEG); 2.478 (t, 2H, CH2CO on PEG); 1.467 (m, 15H, lysine side chain alkyl methylene groups plus t-butyl ester). Quantitative NMR purity=96.8%

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 581065-95-4.

Reference:
Patent; UNIVERSITY OF WASHINGTON; QUANTA BIODESIGN, LTD.; Davis, Paul D.; Wilbur, D. Scott; US2013/52130; (2013); A1;,
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Adding some certain compound to certain chemical reactions, such as: 4341-76-8, name is Ethyl 2-butynoate, 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 4341-76-8. 4341-76-8

General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3¡¤H2O (2 ¡Á 5 mL), distilled water (5 mL), and acetone (2 ¡Á 5 mL) and reused in the next run. The filtrate was washed with water (2 ¡Á 10 mL) and brine (2 ¡Á 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.

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 Ethyl 2-butynoate.

Reference:
Article; Hu, Wenli; Yang, Weisen; Yan, Tao; Cai, Mingzhong; Synthetic Communications; vol. 49; 6; (2019); p. 799 – 813;,
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A common heterocyclic compound, 140-39-6, name is p-Tolyl Acetate, molecular formula is C9H10O2, 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. 140-39-6.

NBS (13.91 g, 0.12 mol, 0.9 eq) and AIBN (2.17 g, 0.01 mol,0.1 eq) were placed in a Schlenk flask and put under an argonatmosphere. CHCI3was added followed by p-toy acetate (19.67 g, 0.13 mol). The mixture was refluxed for 4 h. After cooling down the volume of the mixture was reduced on rotavap to approximately a third and the suspension was filtered. 200 mL of CHCI3was added to the filtrate and it was 3x washed with 80 mL of water, the combined organic layers were dried with MgSC>4, filtered and volatiles were removed on rotavap. 5 mL of AcOEt was added, the mixture was shortly sonicated and while stirring, 40 mL of hexane was added causing precipitation. The mixture was put to a freezer overnight and then filtered washing the white solid with 25 mL of hexane giving 12.05 g (41 %, 0.05 mol) of the product. It was stored in the freezer. The NMR spectrum was in accordance with the literature (J. Org. Chem. 1981, 46 (15), 3029-3035)

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

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; VAVRA, Jan; TICHY, Toma?; MAJER, Pavel; JANCARIK, Andrej; TENORA, Luka?; (148 pag.)WO2018/94334; (2018); A1;,
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40800-65-5, A common compound: 40800-65-5, name is Ethyl 4-amino-3-methylbenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of ethyl 4-amino-3-methylbenzoate (7.43 g)in DMF ..(35 ml) were added DMAP (506 mg) and acetic anhydride(4.66 g) at ambient temperature. After stirring for 4 hours,the reaction mixture was diluted with water (40 ml) andextracted with EtOAc (4 x 60 ml). The combined organicextracts were washed with saturated NaHCOs (2 x 30 ml) andbrine (3 x 100 ml) . The organic layer was dried over MgSC>4 andfiltered. Evaporation gave a residue which was triturated withEtOAc – n-hexane to give ethyl 4-(acetylamino)-3-methylbenzoate(4.324 g) as white crystals. The filtrate was evaporated andtriturated with EtOAc – n-hexane to give second crop (1.64 g).NMR(DMSO-d6,8) :. 1.31 (3H, t, J = 7.1Hz), 2.11 (3H, s) , 2.28(3H, s), 4.29 (2H, q, J = 7.1 Hz), 7.7-7.8 (3H, m), 9.37 (1H,br s) .MS: 244 (M+Na). .

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, Ethyl 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAICEL CHEMICAL INDUSTRIES, LTD.; WO2004/108686; (2004); A2;,
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Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, 25597-16-4

The resulting product (0.50, 2.6mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (1.7g, 10.1mmol) and anhydrous potassium carbonate (0.36g, 5.6mmol) were dissolved in DMF (20mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.50g of the product (50%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.65(s, 1H), 7.16 (s, 1H), 7.07(s, 1H), 5.73(m, 1H), 4.30(m, 2H),1.27(m,3H)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (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. 82911-71-5, name is (9H-Fluoren-9-yl)methyl 1H-benzo[d][1,2,3]triazol-1-yl carbonate, A new synthetic method of this compound is introduced below., 82911-71-5

4-[Bis(tert-butyl)phosphonomethyl]-N-Fmoc-DL-phenylalanine (Compound No. 4) A solution of amine compound No. 3 (770 mg, 1.93 mmol) in dioxane (10 mL) is stirred at room temperature 20 min) with aqueous 1 N NaOH (10 mL, 10 mmol, 5 equiv.). Carbon dioxide is then bubbled in (resulting pH 8.0-8.5) and Fmoc-OBT (857 mg. 2.40 mmol, 1.2 equiv) is added as a suspension in dioxane (3*10 mL) and stirred overnight at ambient temperature. The reaction mixture is partitioned between cold aqueous 5% citric acid (200 mL) and CHCl3 (3*100 mL); the combined organic is washed with cold 5% citric acid (1*100 mL); brine (1*200 mL); dried (MgSO4) and taken to dryness, yielding a light yellow resin (1.92g). The resin is taken up in CHCl3 and filtered through a silica pad. Unreacted Fmoc-OBT and faster impurities are removed with CHCl3 (5*100 mL) with product then being eluted (8*100 mL) with 1% EtOH in CHCl3 and taken to dryness, providing a foam (953 mg) which is dissolved in Et2 O (5 mL) and cooled with petroleum ether (20 mL) to yield compound No. 4 as a white powder: 835 mg (73%); mp 65-70 C. (gas, dec.).

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; The United States of America as represented by the Secretary of the Department of Health and Human Services; US5264607; (1993); A;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 18595-18-1

Example 1 A Preparation of 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(dimethylcarbamoyl)-1H- indazol-3-yl)cyclohex-3-enecarboxylic acid (1A) Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2). Methyl 3-amino-4-methylbenzoate (A-l) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and the mixture was stirred overnight. The half of the solvents were evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc(3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N202, [M+H]+: 177, found: 177.

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); A1;,
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13831-03-3, 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. 13831-03-3, name is tert-Butyl propiolate, This compound has unique chemical properties. The synthetic route is as follows.

To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.

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; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
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A common compound: 106614-28-2, name is Methyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 106614-28-2

To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 C, filtered and dried to give163g of pale white solidRate of 76.5%.HPLC purity 98%.

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, 106614-28-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Keyao Pharmaceutical Technology Co., Ltd.; Zhou Junming; (10 pag.)CN107089981; (2017); A;,
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Some common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, molecular formula is C7H15NO2, 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. 5616-81-9

B. Synthesis of Intermediate B5 Intermediate B5 was synthesized using the method reported in Bioorganic & Medicinal Chemistry Letters 2008, 18, 3902-3905, with modifications as shown in the above scheme. Observed ESI HRMS: m/z 992.3193 [M+H]+. The 1H NMR spectrum of B5 is shown in FIG. 42a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5616-81-9, its application will become more common.

Reference:
Patent; Sirenas LLC; MACHERLA, Venkat Rami Reddy; SCHAMMEL, Alexander Wayne; USUI, Ippei; STOUT, Elizabeth Paige; BEVERAGE, Jacob Neal; LEE, Bryan Junn; COHEN, Steven Bruce; (304 pag.)US2017/15710; (2017); A1;,
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