Category: esters-buliding-blocks

A common heterocyclic compound, 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, molecular formula is C4H7NaO4S, 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. 90030-48-1.

Methyl 3 -( 1 -((2-(trimemylsilyl)ethoxy)methyl)- 1 H-pyrrolo [2,3 -b]pyridin-5- ylsulfonvDpropanoate (4-lb) To a nitrogen gas purged sealable vial of 5-bromo-l-((2-( methylsilyl)ethoxy)methyl)-lH-pyrrolo[2,3-b]pyridine 4-la (3000 mg, 9.17 mmol), copper(i) iodide (6983 mg, 36.7 mmol) and sodium 3-methoxy-3-oxopropane-l-sulfinate(TYGER) (6385 mg, 36.7 mmol) was added DMSO (15 ml) . The reaction mixture was heated in an oil bath at 105c for 18hrs. LCMS analysis showed reaction to be a mixture of desired ester and acid. The reaction was quenched into ethyl acetate (200 ml) and water (200 ml) and the ph adjusted from 7 to 3 with IN HC1. The reaction was filtered thru celite and sand and the filtrate layers separated. The organic which contained a mix of acid and ester was dried over sodium sulfate, filtered and concentrated to an oil. The oil was azeotroped with toluene to remove any remaining water to give a brown oil, 3.4 gms. The oil was dissolved in dichloromethane (20 ml) and methanol (20.00 ml) cooled to 0C and TMS-Diazomethane (4.94 ml, 9.88 mmol) slowly added dropwise. The reaction was stirred at 0C for 10 minutes, quenched with aq. KHSO4 and allowed to stir at room temperature for 1 hr. The reaction was concentrated to remove methanol and the product extracted into ethyl acetate (100 ml), dried over sodium sulfate and concentrated to oil . The oil was chromatographed on silica (100 g, 0-50% ethyl acetate/hexanes) to give the product 4-lb as oil, 1.46 g . LRMS (ESI) m/z 399.1 [(M+H)+; calcd for C17H26N205SSi: 399.1 ].

The synthetic route of Sodium 3-methoxy-3-oxopropane-1-sulfinate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUTCHER, John, W.; WITTER, David; DINSMORE, Christopher; KIM, June; HENDRIX, John; ARCHARYA, Raksha; AHEARN, Sean, P.; JUNG, Joon; RIVKIN, Alexey; JONES, Philip; WO2013/52355; (2013); A1;,
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Adding some certain compound to certain chemical reactions, such as: 2876-78-0, name is Methyl 1-Naphthaleneacetate, 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 2876-78-0. 2876-78-0

alpha-(N-tert-Butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester alpha-(1-Naphthyl)-acetic acid methyl ester (150 mg, 0.75 mmol) was dissolved in tetrahydrofuran. To the solution, hexamethylphosphoramide (HMPA, 671 mg, 3.75 mmol) was added, and the mixture was cooled to -78 C. To this solution, lithium diisopropylamide (1.5 M solution in cyclohexane, 0.75 ml, 1 mmol) was added dropwise, and the mixture was stirred at -78 C. for 30 minutes. Then, a tetrahydrofuran solution (2 mL) of N-tert-butoxycarbonyl-6-amino-1-iodohexane (270 mg, 0.82 mmol) was added dropwise thereto, and the mixture was stirred at -78 C. for 1 hour. The temperature of the reaction solution was raised to 0 C. over 15 minutes, and then, water (50 mL) was added to the solution, followed by extraction with ethyl acetate (50 mL) twice. The organic layer was washed with a saturated ammonium chloride solution (20 mL) and subsequently brine (20 mL) and then dried over sodium sulfate to dryness under reduced pressure. The reaction product was purified by silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain alpha-(N-tert-butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester (271 mg, yield: 91%): 1H NMR (400 MHz, CDCl3): delta 8.11 (d, J=8.5 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.40-7.54 (m, 4H), 4.71 (s, 1H), 4.36 (t, J=7.8 Hz, 1H), 3.61 (s, 3H), 3.04 (m, 2H), 2.07 (m, 2H), 1.24-1.48 (m, 17H); 13C NMR (100 MHz, CDCl3): delta 174.7, 155.9, 135.3, 133.8, 131.3, 128.8, 127.5, 126.1, 125.4, 125.3, 124.6, 122.8, 78.7, 51.8, 46.5, 40.3, 32.9, 29.7, 28.9, 28.2, 27.6, 26.3; FAB-MS: m/z [M+H]+ 400.

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 Methyl 1-Naphthaleneacetate.

Reference:
Patent; TOHOKU UNIVERSITY; KAKE EDUCATIONAL INSTITUTION; KANAGAWA PREFECTURAL HOSPITAL ORGANIZATION KANAGAWA CHILRDEN’S MEDICAL CENTER; ABE, Takaaki; TOMINAGA, Teiji; HAYASHI, Kenichiro; OSAKA, Hitoshi; US2015/353489; (2015); A1;,
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A common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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. 105-53-3.

General procedure: PhIO (550 mg, 2.5 mmol), Et3N¡¤5HF (800 mg, 4 mmol), and DCE (1 mL)were placed in a Teflon test tube. After stirring at r.t. for 15 min, the appropriate malonic ester 1 (1 mmol) and DCE (1 mL) were added. The test tube was sealed with a septum rubber and heated at 70 C for 24 h with stirring. The reaction mixture was neutralized with aq NaHCO3 and the product was extracted with CH2Cl2 (3 ¡Á 10 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. The product was purified by column chromatography on silica gel with hexane-CH2Cl2 as eluent.

The synthetic route of Diethyl malonate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kitamura, Tsugio; Muta, Kensuke; Oyamada, Juzo; Synthesis; vol. 47; 20; (2015); p. 3241 – 3245;,
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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. 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 1459-96-7

To the stirred solution of dimethyl bicycle [2.2.2] octane-1, 4-dicarboxylate (6.35 g, 28.1 mmol) in MeOH (60 mL) and Water (12 mL) was added barium hydroxide octahydrate (4.43 g, 14.03 mmol) and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water (150 mL) and extracted with hexane (2 x 100 mL). The aqueous layer was acidified with 1.5 N HC1 and extracted with EtOAc (2 x 200 mL). The organic layer was dried over Na2S04and concentrated under reduced pressure. The residue was stirred with toluene (100 mL) and filtered. The filtrate was concentrated under reduced pressure to yield 4-(methoxycarbonyl) bicycle [2.2.2] octane- 1 -carboxylic acid (3.5 g, 16.49 mmol, 58.8 % yield) as white 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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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24398-88-7, Adding some certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, 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 24398-88-7.

3-bromobenzoicacid ethyl ester 25 (1.5g, 6.6mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (1.3g,26mmol), after the addition was complete, it was stirred at room temperaturefor 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 26 (1.1g, 78%), without purification into the next step.

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 24398-88-7.

Reference:
Patent; Jiangshu Alpha Biopharmaceuticals, Inc.; Jiangnan University; Nanjing Drum Tower Hospital; Feng, Bainian; Yang, Guijun; Tang, Chunlei; Wang, Guping; Jie, Desheng; (36 pag.)CN105481765; (2016); A;,
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110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 3-mercapto-5-trifluoromethyl-benzoic acid methyl ester (990 mg, 4.19 mmol) in acetonitrile (25 mL) were added N,N-diisopropylethylamine (1.08 g, 1.46 mL, 8.38 mmol) and tert-butyl 4-bromobutanoate (935 mg, 4.19 mmol, CAS RN 110611-91-1). The clear yellow solution was stirred at room temperature for 2.5 hours and then poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow liquid (1.27 g, 80%). MS (ESI+): m/z=379 ([M+]).

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, tert-Butyl 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Erickson, Shawn David; Mattei, Patrizio; Richter, Hans; US2013/267519; (2013); A1;,
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4897-84-1, 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. 4897-84-1, name is Methyl 4-bromobutanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl-4-bromobutyrate in DMSO (0.6 M) was added with stirring NaN3 (1.5 eq). The suspension was heated (45-50 0C, oil bath) with stirring for 5 h. After cooling, H2O was added and the mixture extracted with Et2O. The organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the crude oil used without further purification (99percent).

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; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2009/10783; (2009); A1;,
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105-53-3, A common compound: 105-53-3, name is Diethyl malonate, 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.

Diethyl malonate (20 g, 0.125 mol), triethylamine (25.3 g, 0.25 mol), magnesium chloride (11.9 g, 0.125 mol), acetonitrile (200 ml) were placed in a reaction flask, and the temperature was lowered to -5. C, slowly add acetyl chloride (10g, 0.125mol), temperature control -5C, about 30min drop, after lh incubation, rose to room temperature for 8h. After TLC monitoring reaction, adjust the pH to about 3 with 1N HCl, extract twice with ether, combine the organic phase, wash with 1N HCl, no Dry with sodium sulfate, evaporated to dryness, and the residue was dissolved with DMF.Add bromoethane (16.2 g, 0.148 mol), potassium carbonate (21 g, 0.149 mol), potassium iodide (2.1 g, 0.012 mol), and react at 60 C for 2 h. After the reaction was completed by TLC, the reaction mixture was cooled to room temperature and water was added. , ether, stirring, layering,The organic layer was washed with saturated brine.Dry and evaporate to give a yellow oil, 22 g.Purification by column chromatography gave 7.4 g of pale yellow oil.Yield: 25.8 %.

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, Diethyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang Hainuowei Pharmaceutical Technology Co., Ltd.; Wang Shaojie; Mao Qing; Zhang Bing; (30 pag.)CN110156698; (2019); A;,
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A common compound: 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, 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. 18013-97-3

Under nitrogen protection,Diethyl 2,5-dibromoterephthalate (2g, 5.26mmol), compound 1 (7.03, 13.68mmol), and dry toluene (40mL) were added to a 100mL two-necked flask, and nitrogen was bubbled through to remove it. After half an hour of oxygen, Pd (PPh3) 4 (116 mg, 0.1 mmol) was quickly added, and the reaction solution was heated to 110 C and refluxed for 24 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, and the toluene solvent was distilled off with a rotary evaporator. It was then separated and purified with a chromatography column using petroleum ether / dichloromethane as the eluent (volume ratio of 3: 2) to obtain Compound 2 (2.85 g, 81.2%) as a brown solid.

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, 18013-97-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Science and Technology; Yu Jiangsheng; Tang Weihua; Zhang Zhuohan; Liu Xin; Zhou Jie; Geng Renyong; Yang Linqiang; (25 pag.)CN110606856; (2019); A;,
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Adding some certain compound to certain chemical reactions, such as: 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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 369-26-6. 369-26-6

Step 2: Preparation of methyl 4-fluoro-3-(methylsulfonamido)benzoate (55) A solution of methyl 3-amino-4-fluorobenzoate (0.970 g, 5.73 mmol) in dry pyridine (12 ml), was cooled to 0¡ã C. and methanesulfonyl chloride (0.577 ml, 7.45 mmol) was added drop wise. The resulting mixture was allowed to warm to room temperature and stirred for 3 hours. The solvent was evaporated and the residue was partitioned between DCM and aq. NaHCO3 sat. sol. The organic layer was washed with brine and dried over Na2SO4; the solvent was evaporated and the residue was purified by flash chromatography on silica gel column (ethyl acetate:petroleum ether: 35:65) affording methyl 4-fluoro-3-(methylsulfonamido)benzoate as an off white powder (0.400 g, 1.618 mmol, 28.2percent yield, MS/ESI+ 248.1 [MH]+).

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 Methyl 3-amino-4-fluorobenzoate.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Esposito, Oriana; Carzaniga, Laura; Capaldi, Carmelida; US2014/155391; (2014); A1;,
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