Category: esters-buliding-blocks

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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H10O3

Example 3 3,6,14-Tris(cyclopropylcarboxy)oxymorphone A suspension of oxymorphone (1.56 g; 5.19 mmol), cyclopropylcarboxylic acid anhydride (4.0 g; 25.95 mmol), and toluene (20 mL) was stirred at 80 C. for 160 min. Then DABCO was added in one portion (1.16 g; 10.38 mmol) and the resulting mixture was stirred at 80 C. over 15 h. After this time the conversion was incomplete and an additional amount of anhydride (1.60 g; 10.38 mmol) was added and mixture was stirred at 80 C. for 5 h. Then the reaction mixture was allowed to cool down, concentrated in vacuo, and the excess anhydride was removed under high vacuum. The mixture was diluted with dichloromethane (20 mL), washed with sat. NaHCO3 (5 mL) and the aqueous layer was extracted with dichloromethane (3*5 mL). Combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. Column chromatography (eluent EtOAc?EtOAc+10% MeOH) afforded 2.37 g (90%) of the title compound as a white solid. This reaction could also be performed using cyclopropylcarboxylic acid chloride (less expensive) and triethylamine in ethyl acetate as the solvent at 80 C. to obtain 92% of the titled compound. mp 158-160 C. (EtOH); Rf 0.40 (ethyl acetate:hexane/1:1); [alpha]22D=-122.96 (c=1.0, CHCl3); IR(CHCl3) v 3025, 2934, 2849, 1743, 1716, 1440, 1387, 1100, 1032 cm-1; 1H NMR (600 MHz, CDCl3) delta 6.86 (d, J=8.2 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 5.42 (dd, J=6.0, 1.6 Hz, 1H), 5.08 (s, 1H), 4.22 (d, J=6.0 Hz, 1H), 3.21 (d, J=18.8 Hz, 1H), 3.05 (dd, J=18.3, 6.2 Hz, 1H), 2.55 (dd, J=18.8, 6.2 Hz, 1H), 2.47 (dd, J=11.8, 4.7 Hz, 1H), 2.38 (ddd, J=12.3, 12.3, 5.2 Hz, 1H), 2.31 (s, 3H), 2.22 (ddd, J=12.0, 12.0, 3.4 Hz, 1H), 2.04 (d, J=18.4 Hz, 1H), 1.87 (m, 1H), 1.77-1.69 (m, 1H), 1.65-1.58 (m, 2H), 1.21 (m, 1H), 1.18 (m, 1H), 1.14-1.09 (m, 3H), 1.05 (m, 1H), 1.04-1.00 (m, 2H), 0.99-0.94 (m, 2H), 0.90-0.82 (m, 2H); 13C NMR (150 MHz, CDCl3) delta 174.08, 173.21, 172.47, 147.37, 143.85, 133.30, 131.59, 130.69, 122.69, 118.87, 116.56, 86.88, 81.02, 57.45, 47.06, 45.07, 42.87, 30.28, 27.27, 22.96, 14.52, 12.97, 12.81, 9.367, 9.23, 9.16, 9.05, 8.55, 8.43; MS (+EI) m/z (%): 41 (48), 56 (55), 69 (100), 86 (100), 124 (20), 167 (16), 437 (16), 505 (12); HRMS calcd for C29H31NO7 505.2101. found 505.21049.

According to the analysis of related databases, 33993-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brock University; US2012/283444; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55666-42-7,Some common heterocyclic compound, 55666-42-7, name is tert-Butyl 2-bromobenzoate, molecular formula is C11H13BrO2, 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.

The crude intermediate (2b) (109.6 g, 426 mmol) and 3-fluoro-4-methylphenyl-boronicacid (72.2 g, 449 mmol) were suspended in isopropyl alcohol (360 mL, 4.7 mmol). A 2.0M solution of sodium carbonate in water (360 mL, 720 mmol) was added and the mixture was degassed under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (4.9 g, 4.3 mmol) was then added and the mixture was stirred at 90 C. for 46 hours. The mixture was cooled to room temperature, diluted with EtOAc (800 mL), and the layers were separated. The organic was washed with saturated aqueous NaCl and concentrated under reduced pressure. The recovered oil was purified by silica gel chromatography (3×4-6% EtOAc :hexanes) to yield intermediate (2c) as a clear oil (93.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 2-bromobenzoate, its application will become more common.

Reference:
Patent; Zhang, Weijiang; Colson, Pierre-Jean; Fass, Gene Timothy; US2011/77411; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 57267-03-5, A common heterocyclic compound, 57267-03-5, name is Ethyl 2,2,2-triethoxyacetate, molecular formula is C10H20O5, 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.

2,5-Diamino-benzene-1 ,4-dithiol hydrochloride (5.00 g; 20.39 mmol; 1.00 eq.) is suspended in anhydrous N,N-dimethylformamide (37 cm3) at 50 C. Anhydrous pyridine (3.39 g; 3.49 cm3 42.82 mmol; 2.10 eq.) is slowly added and the mixture stirred at 50 00 for 1 hour under a flow of nitrogen. The clear yellow solution obtained is transferred to a flask containing triethoxy-acetic acid ethyl ester (16.62 g; 75.45 mmol; 3.70 eq.) andyttrium(III) triflate (0.57 g; 1 .02 mmol; 0.05 eq.). Slow precipitation is observed. The mixture is stirred at 60 00 for 72 hours under nitrogen. Subsequently, the mixture is cooled to room temperature. The precipitate is isolated by filtration and washed copiously with methanol, yielding the product as a yellow powder (4.07 g, 59.3%).1H NMR (300 MHz, Chloroform-d) 6: 8.84 (5, 2H), 4.60 (q, 4h), 1.52 (t,6H).

The synthetic route of 57267-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; NANSON, Lana; PRON, Agnieszka; KROMPIEC, Michal; (147 pag.)WO2017/157782; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, name: Ethyl 3-(dimethylamino)acrylate

) [1-(5-Bromo-2-chloro- 3-pyridin-3-yI)methanoyl]dimethylaminoacrylic acid ethyl esterA stirred suspension of 2-chloro-5-bromo pyridine-3-carboxylic acid (5 g) in DCM (50 mL) at 2O0C was treated with oxalyl chloride (2.8 mL) and DMF (1 drop). After 1 h the clear solution was evaporated and re-evaporated from toluene (2x). The acid chloride was re- dissolved in toluene (80 mL) and treated with triethylamine (4.7 mL) and ethyl 3- dimethylaminopropenoate (3.94 g). After stirring for 1 h at 9O0C the mixture cooled and poured onto ice. Saturated aqueous sodium hydrogen carbonate (50 mL) was added and the organic layer washed with water and brine, dried (MgSO4) evaporated and the residue purified by chromatography (silica gel, 50-100% Et2O in petroleum ether [b.p. 40-600C]) to give the title compound as a colourless gum, (6.45 g); ESMS m/z 361.0, 363.0, 365.0 [M+H] +, 315.0, 317.0, 319.0 [M-OEt] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(dimethylamino)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, 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 82702-31-6, Application In Synthesis of Methyl 3-bromo-4-fluorobenzoate

Methyl 3 -bromo-4-fluorobenzoate (699 mg, 3.00 mmol), 1 -(4-hydroxy-3 , 5- dimethylphenyl)ethanone (493 mg, 3.00 mmol), and cesium carbonate (1.47 g, 4.50 mmol) were combined in dimethyl sulfoxide (3 mL). The reaction mixture was heated at 100 C for 16 hours, cooled to ambient temperature, and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydroussodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 10-20 % ethyl acetate in heptanes) to provide the title compound (540 mg, 48 %).

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-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 581065-95-4, A common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, molecular formula is C15H31NO6, 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.

(4) 50g of the amino end product obtained in step (3) was added to 100ml of 3M hydrochloric acid,The temperature was raised to 60 C and stirred for 8h.The reaction is over,Adjust PH neutral,Then spin dry,Suction filtration,The filtrate was dried over anhydrous sodium sulfate,Spin dry,35 g of pure product was obtained.NMR data are as follows:

The synthetic route of 581065-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Deng Zeping; Li Hu; Cheng Jia; (8 pag.)CN107235848; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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: 33993-24-7

Example 1; General Procedure for Demethylation/Acylation; Tertiary amine (0.1 mmol, 1.0 eq.) was dissolved in acetic anhydride (1 ml) and Pd(OAc)2 (0.01 mmol, 0.1 eq.) added. The reaction was heated at 80 C. for 15 hours, cooled to room temperature and passed through a plug of silica using CHCl3:MeOH:NH4OH 80:20:1 as eluent. The volatiles were removed in-vacuo, and the residue suspended in NaHCO3. The aqueous phase was extracted with CHCl3, and the combined organic extracts washed with 1M HCl and brine before being dried over magnesium sulphate, filtered and the volatiles removed in-vacuo to yield the acyl product.It will be understood by a person skilled in the art that the above description for Example 1 is provided for the general procedure. The examples shown below in Examples 1a-1j follow the general procedure outlined above, and shown in Scheme I from compound 3 to 7, but include the use of different sources of palladium and different amounts of Pd(OAc)2, where applicable, and the use of different solvents, as indicated in the table below.; Example 2; Reactivity of a Series of Anhydrides; The reactivity of a series of anhydrides was explored following the general procedure outlined in Example 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33993-24-7, its application will become more common.

Reference:
Patent; Brock University; US2009/5565; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 4630-80-2, The chemical industry reduces the impact on the environment during synthesis 4630-80-2, name is Methyl cyclopentanecarboxylate, I believe this compound will play a more active role in future production and life.

Example 2; 4-(4-(Benzyloxy)phenyl)-6-cyclopentyl-1H-pyrazolo[3s4-b]pyridin-3-amine Step 1:[00144] Sodium hydride (1.378 g, 59.9 mmol, 60% suspension in mineral oil) and ethanol (2.0 mL) were added to a solution of methyl cyclopentanecarboxylate (6.14 g, 47.9 mmol) and l-(4-metfaoxyphenyl)ethanone (6,00 g, 40.0 mmol) in THF (200 mL). The mixture was heated to reflux for 11 h, quenched with water (100 mL) and acidified to pH~2 with 1 N HCl. The THF solvent was evaporated in vacuo. The residue was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with hexanes and small amount of toluene and eluting with 0-15% ethyl acetate in hexanes, gave i-cyclopentyl-3-(4-methoxyphenyl)propane~1,3-dione as yellow liquid (5.494 g, 56% yield). MS (ES+) m/z: 247 (M+H); LC retention time: 4.510 and 3.578 min, likely a mixture of keto and enol forms (analytical HPLC Method A).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; JIANG, Bin; LU, Zhonghui; WO2011/19780; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 443-26-5, name is Ethyl 2-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. COA of Formula: C9H9FO2

REFERENCE EXAMPLE 191 Methyl 4-(4-Methoxybenzenesulfonyl)-1-[2-(1-pyrazolyl)phenylcarbonyl]-7-methyl-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate As described for the general reaction of ethyl 2-fluorobenzoate with amines set forth in Tetrahedron, 53, 7557-7576 (1997), ethyl 2-fluorobenzoate was reacted with pyrazole by refluxing N, N-dimethylformamide to give ethyl 2-(1-pyrazolyl)benzoate, as a thick yellow oil. Anal. Calc’d: for C12H12 N2O2: C, 66.7,H, 5.6; N 13.0: Found: C, 66.5:H, 5.4: N, 12.9; Mass spectrum (ES) 217.2 (M+H).

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

Reference:
Patent; American Cyanamid Company; US6544984; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 42122-75-8, These common heterocyclic compound, 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, 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.

Example 1 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-phenylamino-benzamide1.1 2-Chloro-5-Dhenylamino-benzoic acid methyl esterCs2C03 (2.79 g), palladium(ll) acetate (82 mg), 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binaphthalene (228 mg), iodobenzene (0.69 mL) and methyl-5-amino-2-chlorobenzoate (1.13 g) were placed in a flask and flushed with argon. Dioxane (18 mL) was added and the reaction mixture was heated to 100C for 24h. After cooling to RT, it was diluted with Et20, filtered over a pad of celite and the filtrate was concentrated in vacuo. The crude material was purified by CC (Hept/EtOAc 1/0 to 8/2) to give 1.18 g of the titled compound as a light yellow solid.LC-MS (A): tR = 1 .05 min; [M+H]+: 262.55.

The synthetic route of 42122-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; WO2012/114268; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics