Tag: M.W=100-200

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-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.

To 1.0012 g (8.1228 mmol) of pyridine-2-carboxylic acid wasadded 15 mL of thionyl chloride and the reaction mixture wasstirred under reflux for 3 h. Then 1.3425 g (8.1270 mmol) of methyl-4-amino-3-methylbenzoate in 35 mL of chloroformwas added intothe obtained acid chloride. The reactants were stirred under refluxnext 2 h. After chloroform evaporation under vacuum a beigepowder precipitated:(1.5633 g, 5.7839 mmol, yield ca.: 71%, Anal. Calc. C15H14N2O3[%]: C, 66,66; H, 5,22; N, 10,36; Found: C, 66.33; H, 4.90; N, 10.22).The beige crystals occurred after the recrystallization procedurewith the use of 2-propanol. 1H NMR (600 MHz, CDCl3) delta 10.38-10.29 (m, 1H), 8.66-8.62 (m, 1H), 8.53 (d, J 8.5 Hz, 1H),8.31 (d, J 7.8 Hz, 1H), 7.98-7.95 (m, J 8.6 Hz, 1H), 7.95-7.90 (m,J 3.4 Hz, 1H), 7.51 (td, J 7.3, 4.9 Hz, 1H), 3.91 (s, 1H), 2.47 (s, 1H).13C NMR (151 MHz, CDCl3) delta 167.22, 162.35, 150.11, 148.53, 140.62,138.15, 132.11, 129.18, 127.13, 127.07, 125.77, 122.87, 120.01, 77.58,77.37, 77.16, 52.32, 17.96. FT-IR (KBr, cm-1): 3435 n(O-H KBr), 3342n(N-H), 3098, 3062, 2997, 2951, 2905, 2839 n(C-H), 1712, 1698n(C]O), 1609-1440 n(ringC]C), 1292-1095 n(C-O) and (C-N)overlapped, 769, 684, 622 d(C-H ringC]C)oop.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Skokowski, Przemys?aw; Gruszczy?ska, Joanna; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1178; (2019); p. 669 – 681;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2150-38-1, name is Methyl 3,4-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2150-38-1

To a solution of methyl 3,5-trimethoxybenzoate (3) (0.89 g, 4.54 mmol) in absolute ethanol (15 mL), 5.7 mL (117.8 mmol) of hydrazine hydrate 64 % was added. The reaction mixture was kept under reflux for 2 hours, when TLC indi-cated the end of the reaction. Then, the media was poured into ice and the resulting precipitate was filtered out afford-ing the 3,5-trimethoxybenzohydrazide (6) obtained as a white solid in 61% yield. 1H NMR and 13C NMR data were observed to be in agreement with previous reports [31].

The synthetic route of 2150-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Carneiro, Teiliane R.; do Amaral, Daniel N.; Fokoue, Harold H.; Sant?Anna, Carlos M. R.; Porras, Maria L. G.; Oliveira, Augusto C. A.; Cavalcanti, Bruno C.; Pessoa, Claudia; Barreiro, Eliezer J.; Lima, Lidia M.; Letters in drug design and discovery; vol. 15; 7; (2018); p. 778 – 786;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4606-07-9, A common compound: 4606-07-9, name is Ethyl cyclopropanecarboxylate, 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.

Example 126a 3-Cyclopropyl-3-oxopropanenitrile 126a To a solution of acetonitrile (0.34 mL, 6.58 mmol) in THF (3 mL) at -78 C. under N2 protection was added lithium di-i-propylamide (3.3 mL, 2M in THF, 6.58 mmol) drop-wise. The reaction mixture was stirred at -78 C. for 3 h. Then ethyl cyclopropanecarboxylate (0.50 g, 4.38 mmol) in THF (2 mL) was added and the mixture was allowed to warm to room temperature for a period of 1 h. Water (2 mL) was added and the solvent was removed under reduced pressure. Dichloromethane (2 mL) was added and the pH of the mixture was adjusted to 5 with 2N HCl. It was then extracted with dichloromethane (5 mL*2). The combined organic layer was dried over Na2SO4 and concentrated to afford 126a as a yellow oil, which was used in the next step without further purification.

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 cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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. 33993-24-7.

General procedure: To a stirred solution of 7 (107 mg, 0.20 mmol), TEA (82 muL,0.60 mmol) and DMAP (10 mg, 0.08 mmol) in dry DCM (10mL) acetic anhydride (57 muL, 0.60 mmol) was added dropwiseat 0 C. Then, the reaction mixture was allowed to stir at roomtemperature overnight. The mixture was concentrated anddiluted with H2O (20 mL) and extracted with EtOAc (2¡Á10mL). The combined organic layers were washed with H2O(2¡Á20 mL), brine (20 mL), and dried over Na2SO4. The mixturewas cooled to room temperature, slowly diluted with H2O(100 mL) and extracted with EtOAc (2¡Á100 mL). The combinedorganic layers were washed with H2O (2¡Á150 mL), brine(150 mL), dried over Na2SO4 and concentrated. The residuewas purified by flash chromatography using 5% EtOAc inpetroleum ether to yield 77 mg (0.13 mmol, 65%) of product asa white pure solid.

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

Reference:
Article; Wang, Xiao-Yin; Zhang, Shu-Yong; Li, Jing; Liu, Hua-Nan; Xie, Xin; Nan, Fa-Jun; Acta Pharmacologica Sinica; vol. 35; 11; (2014); p. 1463 – 1472;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28868-76-0, name is Dimethyl 2-chloromalonate, 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 28868-76-0, 28868-76-0

a) Dimethyl (o-methylthio)phenoxymalonate was obtained from dimethyl chloromalonate and (o-methylthio)phenol in analogy to Example 1, paragraph c). From 17 g of (o-methylthio)phenol there were obtained 23 g of malonate from toluene-hexane.

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, Dimethyl 2-chloromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5292740; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics