Tag: M.W=100-200

Electric Literature of 2435-36-1, The chemical industry reduces the impact on the environment during synthesis 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, I believe this compound will play a more active role in future production and life.

Step B: Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate. n-Butyllithium (2.5 M in hexane, 419.0 mL, 1048 mmol) was added slowly to a solution of diisopropylamine (152 mL, 1090 mmol) and anhydrous THF (1000 mL) at -78 C (dry ice/acetone) underN2. Next, the reaction was stirred for 0.5 hours at 0 C before cooling to -78 C. DIVIPU (404 mL, 3350mmol) was added via an addition funnel. Then a solution of dimethyl cyclopentane-1,3- dicarboxylate (78.0 g, 419 mmol) and anhydrous THF (300 mL) was added slowly via an addition funnel. The reaction was warmed to 0 C and stirred for 30 minutes, then cooled to -78C and treated with a solution of 1-bromo-2-chloroethane (59.0 mL, 712 mmol) and anhydrous THF (200 mL). The reaction was allowed to warm slowly to room-temperature and was stirred for 12 hours at room-temperature. The reaction was quenched with saturated aqueous ammonium chloride (400 mL). The reaction was diluted with ethyl acetate (500 mL), the organic layer separated, and the aqueous layer was further extracted with ethyl acetate (2 x 500 mL). The combined organic extracts were washed with brine (2 x 300 mL), dried overanhydrous MgSO4, filtered, and concentrated to dryness. The residue was filtered through a pad of silica gel and washed with ethyl acetate (2000 mL). The filtrate was concentrated to dryness and the residue was purified by flash column chromatography (petroleum ether/ethyl acetate, 30 :1 to 20 :1, gradient elution) to provide the title compound (48.5 g, 54%) as white solid. ?H NIVIR (400MHz, CDC13): 3.69 (s, 6H), 2.08 – 1.99 (m, 4H), 1.91 (s, 2H), 1.73 – 1.63 (m, 4H)

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 cyclopentane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis M.; CHAI, Wenying; KOUDRIAKOVA, Tatiana; KRAWCZUK, Paul J.; KREUTTER, Kevin D.; LEONARD, Kristi; RIZZOLIO, Michele C.; SEIERSTAD, Mark; SMITH, Russel C.; TICHENOR, Mark S.; VENABLE, Jennifer D.; WANG, Aihua; (452 pag.)WO2018/112382; (2018); A1;,
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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. 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H6N2O4

Add 2-phenylquinazolin-4(3H)-one (44.4 mg, 0.2 mmol), 5-diazomic acid (74.9 mg, 0.44 mmol), [Cp*IrCl2]2 (3.2 mg, 2 mol%), AgNTf2 (7.8 mg, 0.02 mmol) and 2 mL of MeOH, after reacting at 80 oC for 24 h, it was cooled to room temperature. The reaction solution was concentrated under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (eluent: petroleum ether / acetone = 15/1, v / v) to obtain the target product 65.9 mg, a white solid, with a yield of 90%.

According to the analysis of related databases, 7270-63-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University; Wu Yong; Hai Li; Yu Xinling; Li Jianglian; He Hua; (7 pag.)CN110272392; (2019); A;,
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Electric Literature of 31600-43-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 31600-43-8 as follows.

[00459] Methyl 2-(benzyloxy)acetate (112) (5.5 g, 30.6 mmol) was dissolved in THF (30 mL). LiAlD4 (1.4 g, 35 mmol) was added at 0 C and the reaction mixture was stirred for 3 h. Water (1.4 mL) was added to quench the reaction. 10% aqueous NaOH solution (2.8 mL) and water (4.2 mL) were added. The mixture was filtered through a pad of CELITE, and the precipitate was washed with THF. The filtrate was dried over anhydrous Na2S04, and concentrated to give crude product, which was purified by silica gel chromatography (30% EtO Ac/petroleum ether) to obtain 2-(benzyloxy)-l,l-dideuteroethanol (113) Yield (3.4 g, 74%). LCMS: m/z 177.1 [M+Na]+; tR = 1.40 min.

According to the analysis of related databases, 31600-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; MCCAULEY, Dilara; LANDESMAN, Yosef; GOLAN, Gali; KALID, Ori; SHECHTER, Sharon; WO2015/42414; (2015); A1;,
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Application of 15441-07-3, The chemical industry reduces the impact on the environment during synthesis 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, I believe this compound will play a more active role in future production and life.

d Methyl 3-[2-(2-phenylthioethoxy)ethylaminosulphonyl]propanoate The subtitle compound (2.85 g) was prepared according to the procedure in example 5 part d using 2-(2-phenylthioethoxy)ethanamine hydrochloride (6 g), triethylamine (4 ml) methyl 3-(chlorosulphonyl)propanoate (5.8 g), and dichloromethane (50 ml). Mass spectrum FAB 348 (M+105).

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, Methyl 3-(chlorosulfonyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Astra Pharmaceuticals Limited; US5846989; (1998); A;,
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Application of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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.

Methyl dimethoxyacetate (19.9 g, 148 mmol) and compound C2 (15.6 g, 74.2 mmol) were combined with molecular sieves (16 g), and the mixture was treated with a solution of potassium t-butoxide in THF (1.0M, 150 mL, 150 mmol). The reaction mixture was heated to reflux for about 18 h; it was then filtered, and the collected solid was rinsed with additional THF. The combined filtrates were neutralized with acetic acid and concentrated in vacuo. The residue was purified by silica gel chromatography (Eluant: 5% MeOH in chloroform) to afford C10 as a white solid. Yield: 9.8 g, 33 mmol, 44%. MS (APCI) m/z 295.2 (M+1). 1H NMR (300 MHz, CDCl3) delta 1.91 (br d, J=10.5 Hz, 2H), 2.38 (m, 2H), 3.48 (s, 6H), 3.60 (dd, J=11, 12, 2H), 4.14 (br d, J=11 Hz, 2H), 4.90 (m, 1H), 5.22 (s, 1H), 8.10 (s, 1H), 9.52 (br s, 1H).

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2010/190771; (2010); A1;,
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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H11NO2

To a solution of the benzyl amine (179 mg, 1.08 mmol) and DIPEA (0.45 ml, 2.6 mmol) in CH2Cl2 (5 ml) was carefully added triphosgene (150 mg, 0.51 mmol) and the resulting solution was stirred at room temperature for 20 minutes (Majer, P.; Randad, R.S. J Org. Chem., 1994, 59, 1937-1938). A solution of 4-[(thiophen-3-ylmethyl)-amino]-piperidine- 1-carboxylic acid tert-huty ester (455 mg, 1.53 mmol) in CH2Cl2 (2 ml) was then added and the reaction was stirred at room temperature for an additional 18 hours. The mixture was diluted with saturated aqueous NaHCO3 (25 ml) and was extracted with CH2Cl2 (20 ml X 3). The combined organic solution was washed with brine (50 ml), was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/Et2O, 9:1, increased to 3:1) gave the urea as a light yellow foam (236 mg, 45%). 1H NMR (CDCl3) delta 1.43 (s, 9H), 1.44-1.58 (m, 2H), 1.69-1.79 (m, 2H), 2.71-2.85 (m, 2H), 3.89 (s, 3H), 4.09-4.24 (m, 2H), 4.33 (s, 2H), 4.39 (d, 2H, J= 5.8 Hz), 4.54 (tt, IH, J= 12.0, 3.7 Hz), 4.80 (t, IH, J= 5.7 Hz), 6.95 (d, IH, J= 4.8 Hz), 7.07 (d, IH, J- 1.5 Hz), 7.13 (d, 2H, J= 8.5 Hz), 7.34 (dd, IH, J= 5.0, 2.9 Hz), 7.91 (d, 2H, J- 8.5 Hz).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
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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. 4897-84-1, name is Methyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4897-84-1

A mixture of vanillin (20.0 g, 131 mmol), methyl 4-bromobutanoate (17.5 mL, 139 mmol) and potassium carbonate (27.2 g, 197 mmol) in A V-dimethylformamide (100 mL) was stirred at room temperature for 18 h. The reaction mixture was diluted with water (500 mL) and the title compound (30.2 g, 91%) was obtained by filtration as a white solid. The product was carried through to the next step without any further purification. (1374) NMR (400 MHz, CDCI3) delta 9.84 (s, lH), 7-46-7-37 (m, 2H), 6.98 (d, J=8.2 Hz, lH), 4.16 (t, J=6.3 Hz, 2H), 3.91 (s, 3H), 3.69 (s, 3H), 2.56 (t, J=7.2 Hz, 2H), 2.20 (quin, J=6.7 Hz, 2H); FontWeight=”Bold” FontSize=”10″ C NMR (100 MHz, CDC13) delta 190.9, 173.4, 153-8, 149-9, 130-1, 126.8, 111.6, 109.2, 67.8, 56.0, 51.7, 30.3, 24.2; MS M/Z (EIMS) = 271.9 (M+Na)+, 253 (M+H)+; LCMS (Method A): tR = 6.48 min.

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FEMTOGENIX LIMITED; JACKSON, Paul Joseph Mark; THURSTON, David Edwin; RAHMAN, Khondaker Mirazur; (243 pag.)WO2017/194960; (2017); 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. 50893-36-2, name is 1-Chloroethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Chloroethyl ethyl carbonate

EXAMPLE 16 1-[(Ethoxycarbonyl)oxy]ethyl 2-[3-(2-thienyl)acrylamido]benzoate A mixture of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) and triethylamine (0.2 ml, 1.4 mmol) in dry acetone (10 ml) was stirred at room temperature for 30 minutes. To the solution, 1-chloroethyl ethyl carbonate (214 mg, 1.4 mmol) and sodium iodide (210 mg, 1.4 mmol) were added under ice cooling, and the mixture was heated under reflux for 19 hours. The reaction mixture was filtered by suction and the solvent was removed from the filtrate. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate, then with saturated aqueous sodium chloride, and dried over magnesium sulfate. After removing the solvent, the residue was purified by silica gel column chromatography (developing solvent:benzene:ether=49:1). The second elude was collected. After removing the solvent, the resulted oily product was crystallized with isopropyl ether to give the desired compound (98 mg, yield, 25percent). m.p., 154°-156° C. (white crystals, recrystallized from methanol/tetrahydrofuran/water). IR (KBr, cm-1): 3250, 1755, 1690 (shoulder), 1670 1 H-NMR (CDCl3, delta): 1.32 (t, 3H, –CH2 CH3), 1.67 (d, 3H, –CH(CH3)–), 4.23 (q, 2H, –CH2 CH3), 6.17-8.17 (m, 9H, aromatic hydrogen, vinyl hydrogen, –CH(CH3)–), 8.83 (d, 1H, aromatic hydrogen), 11.13 (brs, 1H, –CONH–)

The synthetic route of 50893-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sawai Pharmaceutical Co., Ltd.; US5006548; (1991); A;,
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These common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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. Recommanded Product: Methyl 3-amino-4-fluorobenzoate

To a solution of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (10 g, 61 .73 mmol) in dichloromethane (300 ml_) was added DMF (2 ml_) and oxalyl chloride (18 g, 141 .73 mmol) at 0-10 °C. The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The solid obtained was added into a solution of methyl 3- amino-4-fluorobenzoate (7) (10 g, 59.17 mmol) and TEA (20 g, 198.02 mmol) in dichloromethane portionwise. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and diluted with of methanol (250 ml_). The solids were collected by filtration and washed with sat. Na2C03 (2×200 ml_) and methanol (2×50 ml_) to yield methyl 4-fluoro-3-(imidazo[1 ,2-a]pyridine-3- carboxamido)benzoate (8) as a light yellow solid.

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

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
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Electric Literature of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4- hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20 0C. After washing with water (2 X 100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to -10 0C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at – 100C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS {m/z) : 245 (M + l).

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

Reference:
Patent; TRANSTECH PHARMA; WO2008/101914; (2008); A2;,
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