Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 5335-05-7, name is Chloromethyl benzoate, 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 5335-05-7, Recommanded Product: Chloromethyl benzoate

A solution of [2- (8, 9-DIOXO-2, 6-DIAZABICYCLO [5.2. 0] non-1 (7)-en-2-yl) ethyl]- phosphonic acid (20.16 MMOL, 5.25 g) in dry DMF (120 mL) was treated with N, N- diisopropylethylamine (80.64 MMOL, 14 ml) for’/2 hour at ambient temperature. Benzoic acid chloromethyl ester (60.49 MMOL, 10.32 g, synthesis described below) was added at ambient temperature under exclusion of moisture. The reaction mixture was heated to 65C for 20 hours. The temperature was then raised to 72C and stirred at 72C for 16 hours after which the reaction was completed. The mixture was cooled to room temperature and partitioned between 10% sodium bicarbonate and ethyl acetate. After separation of the layers the aqueous phase was again extracted with ethyl acetate (6x) until there was no more product in the water phase (by silica gel TLC, 7% 2M ammonia in methanol and 93% chloroform). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was flash chromatographed on 400 g silica gel using a solvent mixture of 1 % 2M ammonia in methanol and 99% chloroform. Gradually the percentage of ammonia in methanol was increased to 7% and 93% chloroform. The solvent was evaporated in vacuo to yield the desired product (10.5 g, 99%; glass like material). MS (ES-): m/e 527 (M-H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Chloromethyl benzoate, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; WO2004/92189; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 2150-38-1 as follows. Product Details of 2150-38-1

(1) Preparation of 3,4-dimethoxybenzoylacetonitrile Dry acetonitrile (1.8 ml) was added to a solution of n-butyl lithium (a 2.5M solution in hexane, 13.8 ml) in dry THF (30 ml) at -78 C., and the mixture was stirred at the same temperature for 1 hour. To the mixture was added a solution of methyl 3,4-dimethoxybenzoate (6.42 g) in dry THF (15 ml), and the mixture was stirred at -78 C. for 3 hours and then at room temperature for 1 hour. After adding water (100 ml), the reaction solution was extracted with ethyl ether (100 ml). After the aqueous layer was acidified with 6 N hydrochloric acid, it was extracted with ethyl acetate (200 ml*3). The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. Then the solvent was distilled away under a reduced pressure. The resulting residue was crystallized from ethyl acetate/hexane to obtain the title compound (3.6 g) as pale yellow crystals. 1 H-NMR (CDCl3) delta: 3.95 (3H, s), 3.97 (3H, s), 4.03 (2H, s), 6.92 (1H, d, J=9.0 Hz), 7.49 (1H, d, J=9.0 Hz), 7.51 (1H, s)

According to the analysis of related databases, 2150-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US6043246; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0586] Preparation of 53 [0587] To a solution of 52 (0.08 g, 0.395 mmol) in CH2Cl2 (3 mL), added pyridine (74 muL) and methyl 3-(chlorosulfonyl)propanoate (0.1 g, 0.544 mmol). Reaction mixture was stirred for 16 h at rt. and then poured in 10% HCl solution followed by extraction with CH2Cl2. Organic layer was dried and evaporated to obtained 53 (52mg, 34%).

The synthetic route of Methyl 3-(chlorosulfonyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cambridge Enterprise Limited; Kapadnis, Prashant Bhimrao; Glen, Robert; Hiley, Robin; Bell, James; Spring, David; US2013/53372; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 17205-02-6,Some common heterocyclic compound, 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, molecular formula is C7H12O3, 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 solution of ethyl 3-hydroxycyclobutanecarboxylate (10.2 g, 78.4 mmol) in dry pyridine (56.5 mL) at 0 C., TsCl (14.9 g, 78.4 mml) was added portion-wise. The resulting mixture was stirred at rt overnight. The reaction mixture was concentrated in vacuo and the residue obtained was dissolved in EtOAc (100 mL) and sequentially washed with 2 N HCl (100 mL), saturated NaHCO3 (100 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to obtain ethyl 3-(tosyloxy)cyclobutanecarboxylate as a pale yellow oil, which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-hydroxycyclobutanecarboxylate, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Cheung, Wing S.; Huang, Hui; Patch, Raymond J.; US2014/364413; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 40872-87-5, 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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 Synthesis of 3-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester (13) A 100 mL three neck flask equipped with a thermocouple, condenser and stir bar was purged with argon. 3-Amino-4-chlorobenzoic acid methyl ester (5.0 g, 26.94 mmol), 2-cyclopentylethynyl-pyridine (5.528 g, 32.33 mmol), Pd(OAc)2 (181 mg, 0.81 mmol), DtBPF (767 mg, 1.62 mmol), K2CO3 (9.29 g, 67.35 mmol) and NMP (25 mL) were then charged. The reaction was heated to 130 C. and monitored by HPLC. The reaction was complete after 6 hours. The reaction was cooled to room temperature. DMC (11.4 mL, 134.69 mmol) and tetrabutylammonium bromide (TBAB) (0.868 g, 2.69 mmol) were added. The mixture heated to 130 C. HPLC showed less than 3% starting material remaining after 4.5 h. The mixture was filtered through a pad of diatomaceous earth. The black cake was washed with i-PrOAc (50 mL). Solution yield of this mixture was 78%. The crude product residue was dissolved in i-PrOAc (50 mL). The solution was washed with 0.3 N aqueous HCl three times (20 mL, then 2*15 mL). The organic phase was concentrated under vacuum. Propanol, water and 50% NaOH were added to the above residue. The reaction was heated to 90 C. for 1 h. HPLC showed that the reaction was complete. After the mixture was cooled to 50-60 C., diatomaceous earth and activated carbon were added. The mixture was stirred at 50 C. for 30 min and filtered to a 100 mL three neck flask through a pad of diatomaceous earth. The wet cake was washed with 18 mL of water/1-propanol 9/1. The mixture was then heated to 50 C. Acetic acid was added dropwise at this temperature. Precipitation was observed upon the addition. The suspension was then heated to reflux and held for 30 min. The mixture was slowly cooled to room temperature for 2 hours. The precipitate that formed was filtered. The wet cake was washed with 10 mL 1-propanol/water (2:1). The yellow solid was dried under vacuum for 2 days. 5.6 g product was obtained. The yield was 62% for three steps with 99.32 A % purity. 1H NMR (300 MHz, DMSO-d6) delta 8.80 (d, J=3.0 Hz, 1H), 8.14 (s, 1H), 8.00 (m, 1H), 7.77 (d, J=6.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.59 (d, J=6.0 Hz, 1H), 7.50 (m, 1H), 3.89 (s, 3H), 3.70 (s, 3H), 3.17-3.11 (m, 1H), 1.90-1.60 (m, 8H).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, 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. Safety of Ethyl (E)-3-Ethoxyacrylate

To a reactor was charged K3PO4 (4104 g granular, 19.3 moles), ethyl 3-amino-lH-pyrazole-4-carboxylate (2000 g, 12.9 moles), and DMF (18.8 kg) and the mixture was agitated. After 20 min, (?)- ethyl 3-ethoxyacrylate, (2230 g, 15.5 moles) was added and the mixture was heated to 110- 115 C internal temperature (IT). After the reaction was judged to be complete based on consumption of starting material, heating was ceased. The mixture was allowed to stir and cool overnight. Aqueous hydrochloric acid (3 M, 13 L) was added over ~ 2 h. DI water (6 L) was added and the mixture was allowed to stir overnight. The mixture was filtered through polypropylene filter cloth (PPFC) and the residue was washed with water (3 x 5 vol, 3 x 10 L). The solid was placed in trays and oven dried under vacuum at 55 C for 3 days and then 45 C for 4 days to constant wei ht of (2553 g 95.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5941-55-9, its application will become more common.

Reference:
Patent; ZHAO, Qian; SPENCER, Stacey; JIANG, Yutong; HAAS, Julia; EARY, Charles Todd; (352 pag.)WO2019/84285; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, molecular formula is C9H9ClO2, 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. category: esters-buliding-blocks

General procedure: 5.2.1 5,6-Dichloro-1,3-dihydro-3-(4-chlorophenyl)-indole-2-one (3) Sodium hydrate 60% (2.85 g, 71.2 mmol) at -10 C and under nitrogen atmosphere was suspended in N,N-dimethylformamide (DMF) (45 ml) before being added to a solution of 1,2-dichloro-4-fluoro-5-nitrobenzene (5 g, 23.8 mmol) and methyl-4-chlorophenyl acetate (4.4 g, 23.8 mmol). in DMF (70 ml) The mixture was stirred at -5 C for 2 h and then allowed to warm up to room temperature. After quenching with ice, an aqueous solution of 10% NH4Cl was added and the mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using column chromatography on silica gel (hexane/EtOAc = 3/1) to give 1,2-dichloro-4-[2-(methy-l-4-chlorophenyl acetate)]-5-nitrobenzene (3.18 g, 36%) as a colourless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57486-68-7, its application will become more common.

Reference:
Article; Puleo, Letizia; Marini, Pietro; Avallone, Roberta; Zanchet, Marco; Bandiera, Silvio; Baroni, Marco; Croci, Tiziano; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5623 – 5636;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3196-15-4, name is Methyl 2-bromobutyrate, A new synthetic method of this compound is introduced below., Formula: C5H9BrO2

Step 2: methyl 2-(2-((4-methylbenzoyl)imino-6-(methylcarbamoyl(2H)-yl)butanoate To a solution of N-methyl-2-(4-methylbenzamido)benzo[d]thiazol-6-carboxamide (185 mg, 0.57 mmol) prepared in Step 1 in N,N-dimethylformamide (2.0 mL) were added potassium carbonate (236 mg, 1.71 mmol) and methyl 2-bromobutyrate (98 uL, 0.86 mmol). The reaction mixture was stirred at 80 C. overnight and cooled to room temperature. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexaneethyl acetate=8/1?1/1, v/v) to give 160 mg of the titled compound as a white solid (Yield: 66%). 1H NMR (CDCl3, 400 MHz) delta 8.20 (s, 1H), 8.08 (d, 2H), 7.90 (d, 1H), 7.27 (d, 1H), 7.18-7.25 (m, 2H), 6.94-6.95 (m, 1H), 5.53 (m, 1H), 3.57 (s, 3H), 2.91 (d, 3H), 2.39-2.46 (m, 2H), 2.34 (s, 3H), 0.82 (t, 3H)

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; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 90030-48-1, 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. 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

methyl 4-bromo-1-methyl-pyrazole-3-carboxylate (508 mg, 2.319 mmol), (3-methoxy- 3-oxo-propyl)sulfinyloxysodium (810 mg, 4.651 mmol), and copper(1+) (Iodide Ion (1)) (1.31 g, 6.878 mmol) were combined in degassed DMSO (3.048 mL). Nitrogen was bubbled through the reaction for another 5 min and then it was sealed and heated to 80 C. The reaction was heated for 48 h then cooled to room temperature. The reaction was diluted with ethyl acetate (25 mL) and NH4Cl (10 mL). A thick precipitate formed which was filtered and discarded. The layers were separated and the organics were washed with a saturated NH4Cl (30 mL) solution, a satd NaHCO3solution (30 mL), and brine (30 mL). The organics were dried over sodium sulfate and evaporated. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexanes to give methyl 4-(3-methoxy-3-oxo-propyl)sulfonyl-1-methyl-pyrazole-3- carboxylate (297 mg, 44%) ESI-MS m/z calc.290.05725, found 291.1 (M+1)+;Retention time: 0.32 minutes

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; VERTEX PHARMACEUTICALS INCORPORATED; ABELA, Alexander, Russell; ALCACIO, Timothy; ANDERSON, Corey; ANGELL, Paul, Timothy; BAEK, Minson; CLEMENS, Jeremy, J.; CLEVELAND, Thomas; FERRIS, Lori, Ann; GROOTENHUIS, Peter Diederik, Jan; GROSS, Raymond, Stanley; GULEVICH, Anton; HADIDA RUAH, Sara, Sabina; HSIA, Clara, Kuang-Ju; HUGHES, Robert, M.; JOSHI, Pramod, Virupax; KANG, Ping; KESHAVARZ-SHOKRI, Ali; KHATUYA, Haripada; KRENITSKY, Paul, John; MCCARTNEY, Jason; MILLER, Mark, Thomas; PARASELLI, Prasuna; PIERRE, Fabrice Jean, Denis; SHI, Yi; SHRESTHA, Muna; SIESEL, David, Andrew; STAVROPOULOS, Kathy; TERMIN, Andreas, P.; UY, Johnny; VAN GOOR, Fredrick, F.; YOUNG, Tomothy, John; ZHOU, Jinglan; (398 pag.)WO2018/107100; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 13412-12-9, A common heterocyclic compound, 13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, molecular formula is C6H11NO2, 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.

Step 2: 2-(4-Bromo-benzoyl)-3-oxo-butyric acid methyl ester To 3-methylamino-but-2-enoic acid methyl ester (5.0 g, 39.1 mmol) in THF (100 mL) was added pyridine (3.7 mL, 47 mmol). The mixture was cooled to 0 C., and 4-bromobenzoyl chloride (8.55 g, 39.1 mmol) in THF (30 mL) was added dropwise over 2 minutes. The reaction was warmed to room temperature over 1 hour and stirred overnight. Aqueous workup provided the title compound.

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; AMIRA PHARMACEUTICALS, INC.; US2012/258987; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics