Month: February 2021

Electric Literature of 117324-05-7,Some common heterocyclic compound, 117324-05-7, name is Ethyl 2-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

A total of 3.84 g of 2-amino-4-fluoro-benzoic acid ethyl ester obtained in Production Example II-7-a was dissolved in 50 ml of pyridine, 1.64 ml of acetyl chloride was added under ice-cooling, and the mixture was stirred for 1 hours. The reaction mixture was diluted with water and was extracted with diethyl ether. The resulting organic layer was washed with 1 N hydrochloric acid and brine, dried over magnesium sulfate, and then evaporated, to give 4.0 g of the title compound.1H-NMR ( 400 MHz, CDCl3 ) d 1.41 ( 3H, t, J = 6.8 Hz ), 2.14 ( 3H, s ), 4.38 ( 2H, q, J = 6.8 Hz ), 6.73 – 6.81 ( 1H, m ), 8.06 ( 1H, dd, J = 8.8, 6.4 Hz ), 8.53 ( 1H, dd, J = 12.0, 2.4 Hz ), 11.3 ( 1H, brs )

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

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 29823-21-0, These common heterocyclic compound, 29823-21-0, name is Ethyl 8-Bromooctanoate, 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 73 Ethyl 8-(4,5-diphenyl-2-oxo-2,3-dihydroimidazol-1-yl)octanoate 4,5-Diphenylimidazol-2-one was treated with ethyl 8-bromooctanoate and potassium carbonate in butanone to give after work-up the title compound, m.p. 78-79 C., Found:C, 73.7;H, 7.4;N, 6.7%;C25 H30 N2 O3 requires: C, 73.9;H, 7.4;N, 6.9%

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; The Johns Hopkins University; US5648373; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 13195-64-7, 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. 13195-64-7, name is Diisopropyl malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1) sodium hydride as catalyst to 830mmol, 200mmol the diisopropyl malonate 440mmol with propargyl bromide was added to 210mL of anhydrous acetonitrile ice-water bath, the reaction was stirred for 8 hours, the product was washed with water, added with ethyl acetate, spin-dry under reduced pressure to give a tan solid product, compound 1;

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, Diisopropyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Normal University; Hu, Yimin; Mao, Chunyan; (10 pag.)CN105523981; (2016); A;,
Ester – Wikipedia,
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. 62451-84-7, name is Methyl 2-(3-(trifluoromethyl)phenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 2-(3-(trifluoromethyl)phenyl)acetate

To a stirred solution of methyl 2-[3-(trifluoromethyl)phenyl]acetate (6.33 g, 29 mmol) in DMF (45 mL) at 0C was added NaH (60%, 1.28 g, 31.9 mmol). The reaction mixture was stirred for 1 hour and then canuulated drop wise into a solution of 2-(4-bromobutoxy)tetrahydropyran (6.88 g, 29 mmol) in DMF (45 mL) also at 0C. The reaction was further stirred at RT for one hour and poured onto an aqueous saturated solution of NH4C1. The product was extracted with EtOAc, and the combined organic phase was dried over Na2S04 and concentrated under vacuo. A column chromatography (Si02, Heptane / EtOAc) gave 7.82 g (72%) of methyl 6-tetrahydropyran-2- yloxy-2-[3-(trifluoromethyl)phenyl]hexanoate as a light yellow oil.

According to the analysis of related databases, 62451-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; SARIE, Jerome Charles; VASTAKAITE, Greta; (61 pag.)WO2018/83050; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate, 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 34837-84-8, Safety of Methyl 2-(4-fluorophenyl)acetate

General procedure: Various methyl benzoate 8A-V (1.0 equiv) reacted with hydrazine hydrate (excess amount) in anhydrous ethanol. The reaction was stirred at 40 ¡ãC for overnight. The ethanol was removed under reduced pressure. The products were purified by recrystallization, which were washed with ethyl ether. The products were obtained as white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kim, Bo-Kyoung; Ko, Hyojin; Jeon, Eun-Seok; Ju, Eun-Seon; Jeong, Lak Shin; Kim, Yong-Chul; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 202 – 216;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6627-89-0, A common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, molecular formula is C11H14O3, 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 2 7-t-Butyloxycarbonylaminoheptanoic Acid 7-Aminoheptanoic acid (20 g., 1.38 * 10-1 moles) was converted to the title compound using the method of Ulf Ragnarrson et al., Org. Syn., 53, 25 (1973), using tetramethylguanidine (17.3 g., 1.49 * 10-1 moles) and t-butylphenylcarbonate (30 g., 1.54 * 10-1 moles) in dimethylsulfoxide (100 ml.) for three days. The product (24 g.) had m.p. 56-58 after recrystallization from ethyl acetate-hexane-ether. Analysis for: C12 H23 NO4. Calculated: C, 58.75; H, 9.45; N, 5.71. Found: C, 59.14; H, 9.61; N, 5.86.

The synthetic route of 6627-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US4133805; (1979); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 4934-99-0, Quality Control of Methyl 3-hydroxycyclobutanecarboxylate

Methyl 3-(tert-butoxy)cyclobutane-1-carboxylate In a 30-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl 3-hydroxycyclobutane-1-carboxylate (200 mg, 1.54 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (771.4 mg, 3.53 mmol, 2.30 equiv) were mixed in dichloromethane (10 mL), to which was added magnesium perchlorate (34.3 mg, 0.15 mmol, 0.10 equiv) at room temperature. The resulting solution was then stirred for 16 h at 40 C. When the reaction was done, it was quenched with 10 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-TLC eluting with ethyl acetate in petroleum ether (50%) to afford methyl 3-(tert-butoxy)cyclobutane-1-carboxylate (200 mg, 70%) as yellow oil. MS: m/z=187.1 [M+H]+.

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

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1127-01-1, 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. 1127-01-1, name is Ethyl 1-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

2,09 g 1-HYDROXYCYCLOHEXANCARBONSaeURE-ETHYLESTER und 3 g der Verbindung gemaess Beispiel XXIV-1 werden im Oelbad auf 120C erhitzt und bis zum Ende der Gasentwicklung verruehrt und dann noch kurz auf 140C erhitzt. Ausbeute : 42 g (59 % der Theorie). 1H-NMR (400 MHz, CD3CN) : No. = 2,58 (q, 2H, CH2-AR), 3,77 (s, 3H, OCH3), 4,05 (m, 2H, O- CH2-CH3) ppm.

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-hydroxycyclohexanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; LUBOS-ERDELEN, Angelika; WO2004/80962; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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. name: Methyl 4-(aminomethyl)benzoate

Step 4. A solution of 5-fluoro-1H-indazole-3-carboxylic acid (0.25 g, 0.74 mmol) in dichloromethane (5.0 mL) was treated with triethylamine (0.083 g, 0.11 mL, 0.82 mmol), 4-dimethylamino pyridine (0.14 g, 1.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.17 g, 0.89 mmol). 4-Aminomethyl-benzoic acid methyl ester (0.16 g, 0.82 mmol) was added. The mixture was stirred at room temperature for 16 hours, then partitioned between diethyl ether and 1N HCl. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), to yield 4-({[1-(4-difluoromethoxy-benzyl)-5-fluoro-1H-indazole-3-carbonyl]-amino}-methyl)-benzoic acid methyl ester as a yellow solid, 0.19 g (54%), m/z (ISP): 484.5 (M+H).

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

Reference:
Patent; Ackermann, Jean; Bleicher, Konrad; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; US2008/103182; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate, 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. Recommanded Product: 2901-13-5

Place aluminum chloride (586 g, 4.4 moles) and methylene chloride (300 mL) in a 2 L 3-neck round bottom flask equipped with an overhead stirrer, dry ice condenser, and nitrogen atmosphere. Cool to 10 C. and add, by dropwise addition, chlorobutyryl chloride (338 g, 2.4 moles), keeping the temperature below 15 C. After addition is complete, add, by dropwise addition, ethyl 2-methyl-2-phenylpropionate (384 g, 2 mol), keeping the temperature below 15 C. After addition was complete, warm the reaction mixture to 22 C. and stir for 1 hour. Raise the temperature to 90 C., stir for 90 minutes, cool to room temperature and slowly pounr into a 6 L stirred flask containing ice/water (4 kg). Filter through a celite precoat, separate the organic phase and wash the aqueous phase with methylene chloride (50 mL). Evaporate the solvent in vacuo to give a mixture of 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-proprionic acid, ethyl ester and 2-[3-(4-chloro-butyryl)-phenyl]-2-methyl-proprionic acid, ethyl ester.

The synthetic route of 2901-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merrell Pharmaceuticals, Inc.; US6348597; (2002); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics