Month: June 2021

Application of 110661-91-1, 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. 110661-91-1, name is tert-Butyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate (20 g, 53 mmol) in DMF (100 mL) at 0 C. was added KOtBu (7.73 g, 69 mmol). The mixture was stirred at 0 C. for 45 minutes, then tert.-butyl 4-bromobutanoate (15.4 g, 69 mmol) was added at 0 C. The reaction mixture was allowed to warm to room temperature and stir overnight. The mixture was portioned between ether and saturated aqueous NH4Cl. The organic solution was washed with water and saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The residue was taken into hot cyclohexane. The mixture was allowed to stand for 72 hours. The solvent was decanted and the residue was washed with cold cyclohexane. The solid was then dried under high vacuum to yield 4-(3-tert.-butoxycarbonyl-propoxy)-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-1a: 20.8 g). 1H NMR (400 MHz, CHLOROFORM-D) ppm 1.4 (s, 9H), 1.4 (t, J=7.1 Hz, 3H), 1.9 (m, 2H), 2.3 (t, J=7.5 Hz, 2H), 4.0 (t, J=5.9 Hz, 2H), 4.4 (q, J=7.1 Hz, 2H), 7.2 (m, 2H), 7.2 (m, 2H), 7.4 (m, 3H), 7.5 (m, 1H); m/z=519.0 (M+1).

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

Reference:
Patent; Pfizer Inc; US2006/241100; (2006); 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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

To a solution of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (0.50 g, 2.5 mmol) in DMF (24.8 ml) at 0 C was added NBS (0.441 g, 2.48 mmol) and this was stirred at 0 C. After 10 minutes the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with EtOAc, washed with water, dried over MgS04, filtered and concentrated. This was purified by flash chromatography (0-15% EtOAc:DCM) to provide the title compound. MS (ESI+) m/z 244.1 , 246.1 (M+H).

The synthetic route of 49851-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Reference of 18448-47-0, 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. 18448-47-0, name is Methyl cyclohex-1-enecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSCt, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).

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 cyclohex-1-enecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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Electric Literature of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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 stirred solution of 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido- )phenoxy)picolinic acid (08) (200 mg, 0.44 mmol, 1.0 equiv) in DMF (5.0 mL, 25.0 vol. equiv.) were added tert-butyl 3-(2-(2-aminoethoxy)ethoxy)propanoate (10) (124 mg, 0.53 mmol, 1.2 equiv), HATU (505 mg, 1.33 mmol, 3.0 equiv) and DIPEA (68.5 mg, 0.53 mmol, 1.20 equiv). The reaction mixture was stirred for 12h at RT. Completion of reaction was monitored by TLC. The Reaction mixture was quenched with DMW (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic extract was washed with brine (100 mL), dried over Na2S04 and concentrated under vacuum to afford the desired compound (11) (290 mg, 98.20%) as a brown gum. MR (300 MHz, OMSO-d6) delta 9.22 (s, 1H), 9.00 (s, 1H), 8.69 (s, 1H), 8.52-8.51 (d, 1H), 8.13-8.12 (d, 1H), 7.65-7.64 (d, 2H), 7.63 (s, 1H), 7.61-7.60 (d, 1H), 7.58 (s, 1H), 7.39-7.38 (d, 1H), 7.19-7.16 (m, 3H), 3.59-3.41 (m, 16H), 2.89 (s, 2H), 2.41-2.39 (d, 2H) 1.40-1.37 (t, 9H). MS (ES+): 755.0 (M+l); MS (ES-): 753.2 (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 tert-Butyl 9-Amino-4,7-dioxanonanoate, its application will become more common.

Reference:
Patent; QUARTZ THERAPEUTICS, INC.; ZAMBONI, Robert; HENNING, Ryan; JI, Alan; SMITH, Tyler; HELLER, Bradley; REDDY, Thumkunta Jagadeeswar; ROCHELEAU, Sylvain; BEAULIEU, Marc Andre; (266 pag.)WO2018/200981; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 2-ethoxy-2-iminoacetate

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (M+H) +

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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140°C for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and the extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane: ethyl acetate = 4:1 -> 2:1) gave 136 mg (58percent) of the desired compound as a colorless amorphous product. 1H NMR (400 MHz, CDCl3) delta 1.77-1.86 (1H, m), 2.11-2.19 (1H, m), 2.60-2.67 (1H, m), 2.71 (3H, s), 3.21-3.38 (4H, m), 3.54 (2H, t, J= 6.1 Hz), 3.87 (3H, s), 6.26 (1H, t, J = 6.1 Hz), 6.78 (1H, t, J = 7.9 Hz), 6.82 (1H, d, J = 8.6 Hz), 7.32-7.36 (1H, m), 7.41 (2H, d, J = 8.6 Hz), 7.63 (1H, dd, J = 1.8, 7.3 Hz), 7.85 (2H, d, J = 8.6 Hz). FAB+(m/z): 470 (M+H).

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; KYORIN PHARMACEUTICAL CO., LTD.; EP1780210; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

541-16-2, name is Di-tert-Butyl malonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 541-16-2

Di-tert-butyl malonate (33.5 mL, 150 mmol) was added dropwise to a stirred suspension of NaH (6.0 g, 60 % suspension in oil, 150 mmol) in 1,2-dimethoxyethane (100 mL) under Ar, cooled in a water-ice bath. After stirring for 10 min, Intermediate 1G (16.2 g, 50 mmol) was added and the reaction was heated at 85 C for 20 h. After this time, acetic acid (100 mL) was added, the reaction flask was fitted with a distillation head and the temperature was raised to 130 C. 1,2-dimethoxyethane was distilled off under atmospheric pressure until the distillate was acidic (-100 mL). The distillation head was removed, a reflux condenser was attached, water (20 mL) was added and the reaction heated at 130 C for 12 h. The reaction was concentrated under reduced pressure and poured onto 200 g of ice and 100 mL of saturated aqueous NaOAc. Intermediate 1H was isolated as a white solid by filtration and further dried by reflxing with toluene in a Dean- Stark apparatus (11.0 g, 76 %). m/z ( +H)+= 288.2.1H- MR (400 MHz; DMSO-d6): delta 12.05 (bs, 1H), 8.79 (d, J= 4.5 Hz, 1H), 8.06 (dd, J= 9.2, 5.8 Hz, 1H), 7.94 (dd, J= 11.0, 2.8 Hz, 1H), 7.66-7.61 (m, 1H), 7.50 (d, J= 4.6 Hz, 1H), 2.41 (d, J= 7.6 Hz, 2H), 2.28- 2.23 (m, 1H), 1.87-1.78 (m, 2H), 1.73-1.64 (m, 6H).

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; SHAN, Weifang; WILLIAMS, David K.; ZHANG, Liping; (87 pag.)WO2019/74822; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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.

Referential Example 23 3.1 mL of triethylamine and 1.3 mL of benzoyl chloride were added to 19 mL of methylene chloride solution containing 1.9 g of methyl 2-amino-4-methoxybenzoate while ice-cooled sequentially and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and chloroform and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 2.6 g of methyl 2-(benzamido)-4-methoxybenzoate as white solid. 1H-NMR (CDCl3) delta: 3.92 (3H, s), 3.93 (3H, s), 6.65 (1H, dd, J = 9.0, 2.7 Hz), 7.51-7.59 (3H, m), 8.00 (1H, d, H = 9.0 Hz), 8.05-8.07 (2H, m), 8.63 (1H, d, J = 2.7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4-methoxylbenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (2007); A1;,
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. 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate

A solution of dimethyl bicyclo [2.2.1] heptane-1, 4-dicarboxylate (500 mg, 2.356 mmol) and LiOH (169 mg, 7.07 mmol) in water (20 mL) and MeOH (10 mL) was stirred at RT for 48 hours. The solution was poured into 1 N HCl and extracted with EtOAc. The combined organic was dried over Na2SO4and concentrated in vacuo to give crude 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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (2016); 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. 5164-76-1, name is Dimethyl pent-2-enedioate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H10O4

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

The synthetic route of 5164-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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