Month: September 2021

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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2,2-dimethoxyacetate

A diethyl ether solution of ethylmagnesium bromide (concentration=2 1.85 mass %, 277 g) was added to a reaction flask and was cooled to around 0 C. by stirring on an ice-cooling bath. A Grignard reaction was carried out by the dropwise addition to this solution over one hour of methyl dimethoxyacetate (25 g). This was followed by return to room temperature and reaction for 12 hours. The reaction solution was ice-cooled; 200 g of a saturated aqueous ammonium chloride solution was added dropwise; and the pH was subsequently adjusted to around neutrality by the dropwise addition of 10 mE of a 36% hydrochloric acid solution. The solution was then transferred to a separatory funnel; the organics were extracted with 50 g of hexane and separated; and drying was carried out over an appropriate amount of magnesium sulfate. This hexane suspension was filtered followed by removal of the solvent on an oil bath at around 65 C. Distillation was performed under reduced pressure on an oil bath at around 100 C. to obtain 22.4 g of a transparent and colorless 3-dimethoxym- ethyl-3-pentanol (GC purity=96.3%). 10 g of pure water and 1 g of 36% hydrochloric acid were added under ice cooling to 7 g of the 3-dimethoxymethyl-3-pentanol and stirring was carried out overnight. After this, 9.5 g of a 33% aqueous ethylamine solution was added dropwise under ice cooling and a reaction was run for 10 hours. The pH of the reaction solution at this time was 10 to 11. When stirring was stopped, separation occurred into an aqueous layer and a small amount of an organic layer, and the organic layer was determined to be alcohol compound No. 140 according to the NMR results. 2.7 g of the target was obtained for a yield of 33%.

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 89-91-8.

Reference:
Patent; ADEKA CORPORATION; SAKURAI, Atsushi; HATASE, Masako; YOSHINO, Tomoharu; ENZU, Masaki; (40 pag.)US2017/129912; (2017); A1;,
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Application of 1130165-74-0, 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 1130165-74-0 as follows.

(1) A mixture of ethyl 4-bromo-3-fluorobenzoate (500 mg), tris(dibenzylideneacetone)dipalladium (0) (94 mg), (R)-(+)-(1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (189 mg), cesium carbonate (1.98 g), (R)-pyrrolidin-3-ol (353 mg), and toluene (5 mL) was stirred for 1 hour under heating and refluxing. The reaction mixture was cooled to room temperature and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent; 70%-30% n-hexane/ethyl acetate] to obtain ethyl (R)-3-fluoro-4-(3-hydroxypyrrolidin-1-yl)benzoate (390 mg) as a brown oily substance. MS (ESI nm/z): 254 (M+H) RT (min): 1.41

According to the analysis of related databases, 1130165-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; Ookubo, Megumi; Sekine, Shinichiro; Mashiko, Tomoyuki; Kawai, Hyoei; Fukunaga, Hirofumi; US2020/17459; (2020); A1;,
Ester – Wikipedia,
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23676-08-6, name is Methyl 4-ethoxybenzoate, 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. category: esters-buliding-blocks

General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.

The synthetic route of 23676-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Jieun; Kim, Kun-Hee; Kim, Dong-Young; Chandrasekaran, Gopalakrishnan; Kim, Minhee; Pagire, Suvarna H.; Dighe, Mahesh; Choi, Eun Young; Bak, Su-Min; Kim, Eun-Young; Shin, Myung-Geun; Choi, Seok-Yong; Ahn, Jin Hee; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
Ester – Wikipedia,
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Related Products of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

5-Ethyl-2-pyrazin-2-yl-thiazol-4-ol: A solution of pyrazine-2-carbothioamide (1 g, 7.19 mmol) in ethanol (20 ml) was treated with methyl 2-bromobutyrate (1.56 g, 992 mul, 8.62 mmol) an pyridine (853 mg, 872 mul, 10.8 mmol) and heated to reflux for 2 hours. The reaction mixture was cooled and concentrated to dryness under reduced pressure, and the resulting solid was filtered and washed with diethyl ether to provide 5-ethyl-2-pyrazin-2-yl-thiazol-4-ol (0.740 g, 50%) which was used directly without further purification. MS (M+H)=208.

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

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

Cesium carbonate ((3.1 g, 9.6 mmol) was added to 2,4-difluorophenol (0.83 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol)In a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was subjected to column chromatography (peel ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(2,4-difluorophenoxy)benzoate (1.58 g, 4. 72%).

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; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Sun Changan; Zhang Xiaoyu; Chen Gangsheng; Zong Shumin; (45 pag.)CN109836385; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 49851-36-7, These common heterocyclic compound, 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, 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.

ln a 40 mL vial, HATU (2.263 g, 5.95 mmol) was added in one portion at room temperature to a DMF solution (10 mL) of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (1g, 4.96 mmol), 6-chloropyridine-2-carboxylic acid (CAS 4684-94-0) (0.938 g, 5.95 mmol) and DIEA (2.165 mL, 12.40 mmol). The resulting solution was allowed to stir at room temperature (2.5 hr). The reaction was diluted with ethyl acetate, washed with water (twice) and a saturated aq. NaCI solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified via FCC (10:1 Heptane/ethyl acetate to 1 :1 Heptane/ethyl acetate) to give the title compound. MS (ESI+) m/z 305.3 (M+H).

Statistics shows that Methyl 2-(2-aminophenyl)acetate hydrochloride is playing an increasingly important role. we look forward to future research findings about 49851-36-7.

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

Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. SDS of cas: 6933-47-7

General procedure: A solution of (7: R1=cyclopentyloxy) (100mg, 363mumol) in dichloromethane (5 mL), cooled to 0C, was treated with oxalyl chloride (63.6 muL, 727 mumol), followed by a drop of N,N-dimethylformamide. The resultant mixture was stirred for 1h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (5 mL) and then treated with a solution of methyl 4-aminobenzoate (8: R2=H, R=Me) (54.9mg, 363mumol) and di-isopropylethylamine (190muL, 1.09mmol) in dichloromethane (5mL). The reaction mixture was stirred for 12 h at room temperature and then partitioned between dichloromethane (20 mL) and aqueous 1M hydrochloric acid (20 mL). The phases were separated, and the organic phase was washed successively with water (2×20 mL), and brine (20 mL), dried over magnesium sulfate, filtered and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (12 g, 0-100 % ethyl acetate/isohexane) to afford methyl 4-[3,5-dichloro-4-(cyclopentyloxy)benzamido]benzoate (10: R1 = cyclopentyloxy, R2 = H, R =Me) (30mg, 20% yield). 1H NMR (400MHz, CDCl3) delta 8.06 (2H, d, J=8.8Hz,), 7.85 (1H, br s), 7.82 (2H, s), 7.71 (2H, d, J=8.8Hz), 5.07-5.03 (1H, m), 3.92 (3H, s), 2.10-1.90 (4H, m), 1.85-1.70 (2H, m), 1.70-1.60 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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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. 35179-98-7, name is Chloromethyl ethyl carbonate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H7ClO3

EXAMPLE 2 Preparation of 4-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl] sulfinyl]-1H-benzimidazole-1-ylmethyl ethyl carbonate To NaOH (0.26 g, 6.5 mmol) dissolved in H2 O (12 ml) 4-fluoro-2-[[(4-methoxy-2-pyridinyl) methyl]sulfinyl]-1H-benzimidazole (1.0 g, 3.3 mmol) and tetrabutylammoniumhydrogen sulfate (1.1 g, 3.2 mmol) were added under stirring. The mixture was stirred for about 5 min, at ambient temperature and then extracted 3 times with CH2 Cl2 (20 ml). After separation the combined CH2 Cl2 phases were dried over Na2 SO4, filtrated and the solvent evaporated off giving an oil. The residual oil was dissolved in toluene (30 ml). Chloromethyl ethyl carbonate (0.68 g, crude material) dissolved in dry toluene (3 ml) was added under a protective gas and under stirring. The mixture was stirred at ambient temperature over night. The toluene was evaporated off and the residual oil was chromatographed on a silica column using ethyl acetate as eluent. Crystallizing from ethyl acetate – diethyl ether gave the title compound (0.33 g, 25%). NMR data for the product is given below.

According to the analysis of related databases, 35179-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aktiebolaget Hassle; US5049674; (1991); A;,
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. 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, A new synthetic method of this compound is introduced below., 90030-48-1

Cu(I)I (570 mg, 3.02 mmol) was added to a solution of 4-((8-(6-bromo-4- methylbenzo[d]thiazol-2-yl)-8-azabicyclo[3.2.l]octan-3-yloxy)methyl)-5-cyclopropyl-3-(2- (trifluoromethoxy)phenyl)isoxazole_(960 mg, 1.51 mmol), sodium 3-methoxy-3-oxopropane- 1-sulfinate (790 mg, 4.54 mmol ) and L-proline (174 mg, 1.51 mmol) in dimethylsulfoxide (20 ml) at room temperature and the resulting mixture warmed to 130 C. After 16 h, water and ethyl acetate were added and the mixture filtered through celite. The filtrate was then washed with cold water, brine, dried over anhydrous Na2S04, filtered, concentrated under reduced pressure and purified by flash column chromatography using silica gel 100-200 mesh, eluting with 0-65% ethyl acetate in petroleum ether to afford the titled compound (0.25 g, 25 %) as a solid. LC-MS: 2.57 mins, [M+H]+ 706

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; INORBIT THERAPEUTICS AB; SHARMA, Rajiv; BENTHEM, Lambertus; JUDKINS, Robert; (69 pag.)WO2020/33382; (2020); 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 55666-43-8 as follows. COA of Formula: C7H13BrO2

Example 6; 7V-Benzyl-3-(4-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-l,2-dihydroquinolin-5- yl)ethyl]amino}piperidin-l-yl)propanamide; i) tert-Butyl 3-(4-oxopiperidin-l-yl)propanoate o To a solution of piperidin-4-one (1 g) in CHCl3 (30 mL) was added fert-butyl 3- bromopropanoate (1.2 mL) followed by triethylamine (1.8 mL). The reaction mixture was heated at reflux for 18 h. The mixture was allowed to cool to room temperature then diluted with EtOAc and H2O and the layers separated. The aqueous material was extracted with further EtOAc (x2) then the combined organic extracts washed with water followed 5 by saturated aqueous NaCl, collected and dried (MgSO4). The volatiles were removed in vacuo to afford the sub-title compound as an orange oil. Yield: 0.92 g 1H NMR (CDCl3) delta 2.81 – 2.75 (m, 6H), 2.47 – 2.42 (m, 6H), 1.46 (s, 9H).

According to the analysis of related databases, 55666-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/102771; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics