Category: esters-buliding-blocks

Reference of 57625-74-8,Some common heterocyclic compound, 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, molecular formula is C11H14O2, 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 C. To a suspension ofAlCl3 (500.0 mg, 3.75 mmol) inCH2Cl2 at-10 C was added dropwise oxalyl chloride (476.0 mg, 3.75 mmol) inCH2C12. The mixture was stirred at this temperature for 30 min. Then a solution of 2-methyl-2- phenyl-propionic acid methyl ester (178.0 mg, 1.0 mmol) inCH2C12 was added. The resulted mixture was stirred at-10 C for 1 hr and rt overnight. The mixture was filtered through a pad of celite, the solvent and excess oxalyl chloride was removed under reduced pressure. The residue was dissolved in chlorobenzene and refluxed for 4 hr. Solvent was removed and the residue was dried to give2- (4- chlorocarbonyl-phenyl) -2-methyl-propionic acid methyl ester.

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-methyl-2-phenylpropanoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99276; (2003); A1;,
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Related Products of 18469-52-8, A common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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.

The compound 2,4-dichloro-6-nitro-quinazoline (0.115 g, 0.47 mmol) was weighed in a reaction flask,Isopropyl alcohol 4mL,Stir into suspension,Methyl p-aminomethylbenzoate (0.094 g, 0.56 mmol) and DIEA (0.106 g, 0.82 mmol) were added,Reaction at room temperature 2.5h.Stop stirring, add dichloromethane to make the reaction solution becomes clear, add silica gel,Concentration by column chromatography [petroleum ether / ethyl acetate = 10: 1 (v / v) / methylene chloride / ethyl acetate = 10: 1 (v / v)] gave 0.162 g of a yellow solid in a yield of 92.6%

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; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Jin Jing; Zhu Lina; Zhang Chongjing; (85 pag.)CN102250075; (2016); B;,
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Related Products of 1150566-27-0, 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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (500.0 mg, 2.21 mmol) in dioxane:EtOH:H2O (4:1:3, 9 mL), (3,5-dimethylisoxazol-4-yl)boronic acid (404 mg, 2.87 mmol), Cs2CO3 (1.45 g, 4.42 mmol) and Pd(PPh3)4 (127.0 mg, 0.11 mmol) were added and the reaction was refluxed for 15 h. After cooling to room temp, the solvents were evaporated and the solid was taken up in THF (6 mL). A solution of LiOH (106.0 mg, 4.42 mmol) in 0 (3 mL) was added, the mixture was stirred for 15 h. The solvent was removed under reduced pressure and the residue was acidified to pH 4 with 3N HCl. The volatiles were evaporated under reduced pressure and the solid was triturated with MuepsilonOmicronEta:0 (1:1). Upon filtration 6-(3,5-dimethylisoxazol-4-yl)imidazo[1,2-b]pyridazine-3-carboxylic acid was obtained (331.0 mg, 58%). MS (ESI) calcd for C12H10N4O3: 258.1; found: 258.9 [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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
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Reference of 15012-36-9,Some common heterocyclic compound, 15012-36-9, name is Methyl 2,3-dimethylbenzoate, molecular formula is C10H12O2, 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 methyl 2,3-dimethylbenzoate (2.0 g, 12.2 mmol) in 1,2-dichloroethane (10 mL) were added chloromethyl methyl ether (5 mL, 36.0 mmol), thionylchloride (0.36 mL, 5.0 mmol) and ferric chloride (0.4 g, 2.4 mmol) at 0 C. The resulting mixture was heated to 55 C for 2 h. After cooling to room temperature, the mixture was extracted with EtOAc (3 x 100 mL) and washed with water (20 mL) and brine (20 mL). The combined organic extracts were dried over anhydrous Mg504, filtered and concentrated.Silica gel chromatography (hexane:EtOAc) afforded the title compound (1.1 g). MS (ES) m/z 213 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,3-dimethylbenzoate, its application will become more common.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); A2;,
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Reference of 59833-69-1, 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. 59833-69-1, name is Methyl 2-(3-amino-4-chlorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 35c (781 mg, 3.9 mmol) and pyridine (0.95 mL, 11.7 mmol) in CH2Cl2 (10 mL) was added a solution of 34a (1.3 g, 3.9 mmol) in CH2Cl2 (10 mL). After stirring overnight at room temperature, the reaction mixture was quenched with water and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (1.3 g, 63% in 2 steps) as a pale yellow amorphous powder.

The synthetic route of Methyl 2-(3-amino-4-chlorophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwahashi, Maki; Naganawa, Atsushi; Kinoshita, Atsushi; Shimabukuro, Atsushi; Nishiyama, Toshihiko; Ogawa, Seiji; Matsunaga, Yoko; Tsukamoto, Kohki; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Oumi, Rie; Odagaki, Yoshihiko; Katagi, Jun; Yano, Koji; Tani, Kousuke; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 22; (2011); p. 6935 – 6948;,
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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 52787-14-1 as follows. COA of Formula: C11H12O4

To a mixture of K2CO3 (1194.5 g), homoterephthalic acid dimethyl ester (600 g) in DMAc (3000 mL), propargyl bromide (582.43 g) was added followed by TBAI (106.41 g) at 25-30 C. and stirred for 20-26 hours. The reaction was monitored by HPLC and found the ratio of Monopropargyl homoterephthalic Acid Dimethyl Ester to that of dipropargyl homoterephthalic Acid Dimethyl Ester to be not less than 85:15. After 26 hours the reaction mixture was quenched with DM water (3000 ml) and extracted with ethyl acetate (2*3000 ml). The organic layer was separated and back-extracted with DM water (3000 ml). The organic layer was then evaporated to dryness at reduced pressure on a rotary evaporator (below 60 C.). Further IPA (1000 ml) was added to the residue and evaporated to dryness at reduced pressure. The crude product was crystallized by dissolving in IPA (000 ml) at 45-50 C. and cooled to 0-5 C. and stirred for 1-2 hours. The product was vacuum filtered. The product obtained was further crystallized with IPA (1800 ml) saturated with Ethyl acetate (54 ml) by dissolving at 55-60 C. and stirred at 20-25 C. for 2-3 hours, followed by stirring at 0-5 C. for 2-3 hours. The solid was filtered and dried under vacuum at 40-45 C. to give 466 g (65.6%) of the title compound. Purity: 99.19%

According to the analysis of related databases, 52787-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fresenius Kabi Oncology Limited; Lahiri, Saswata; Gupta, Nitin; Singh, Hemant Kumar; Panda, Nilendu; Handa, Vishal; Abul, Azim; Gupta, Chandan Kumar; Sanghani, Sunil; Sonavane, Ghanashyam Madhukar; US2015/183789; (2015); A1;,
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Application of 61367-07-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: Methyl (1r,4r)-4-(ethylsulfonamido)cyclohexane-1-carboxylate (0635) (0636) A solution of methyl (1r,4r)-4-aminocyclohexane-1-carboxylate hydrochloride (120 g, 0.62 mol) and Et3N (346 mL, 2.48 mol) in anhydrous DCM (2.5 L) was stirred at RT for 30 min. Ethanesulfonyl chloride (80.6 g, 0.63 mol) was added dropwise over 30 min to the reaction mixture at 0-5 C. After addition, the mixture was stirred at 0 C for 3 h. The mixture was quenched with water (250 mL) at 0 C. After partition, the organic layer was washed with H2O (600 mL, 5 volumes) and 1 N HCl (2 × 600 mL, 2 × 5 volumes), H2O (600 mL, 5 volumes) and brine (600 mL, 5 volumes), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford crude methyl (1r,4r)-4-(ethylsulfonamido)cyclohexane-1-carboxylate (117.6 g, 76%) as a light yellow solid, which was used for the next step without further purification.1H NMR (CDCl3400 MHz): delta 4.36 (d, J = 8.0 Hz, 1 H), 3.67 (s, 3 H), 3.29-3.22 (m, 1 H), 3.04 (q, J = 7.6 Hz, 2 H), 2.25-2.21 (m, 1 H), 2.15-2.09 (m, 2 H), 2.08-2.01 (m, 2 H), 1.58-1.51 (m, 2 H), 1.39-1.25 (m, 5 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
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Related Products of 14062-25-0, 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 14A Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate 1.45 g (36.2 mmol) of sodium hydride in mineral oil (60% pure) were initially charged in 100 ml of DMF. A mixture of 4.0 g (16.5 mmol) of ethyl (4-bromophenyl)acetate and 6.5 g (34.6 mmol) of 1,2-dibromoethane was dissolved in 50 ml of THF and slowly added dropwise. The mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 mum, 250 mm*40 mm (30% methanol/70% water to 100% methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.15 g (26% of theory) of a liquid. GC-MS [Method 5]: Rt=5.45 min; MS(ESIpos): m/z=268/270 (M+) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.09 (t, 3H), 1.16-1.20 (m, 2H), 1.46-1.50 (m, 2H), 4.02 (q, 2H), 7.26-7.31 (m, 2H), 7.47-7.51 (m, 2H)

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, Ethyl 2-(4-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); 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. 122-63-4, name is Benzyl propionate, A new synthetic method of this compound is introduced below., Computed Properties of C10H12O2

Carbapenem Intermediate (CPI) was prepared according to the synthetic scheme shown in Scheme 1. In the first step of the process, benzyl propionate is reacted with isobutoxycarbonyloxy acetic acid methyl ester in a solvent at low temperature in the presence of LDA to form ketoester A. The ketoester A is then contacted with the acetoxyazetidinone B (prepared by any number of known, synthetic routes) in a solvent, and sodium carbonate is added. The reaction ages for a period of time at a temperature such that the reaction goes substantially to completion, generating the target lactam C.

The synthetic route of 122-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOB SYNTHESIS; CHOI, Woo-Baeg; KIM, Deog-Il; GRUSZECKA-KOWALIK, Ewa; JOO, Hyung-Yeul; LIU, Shuangpei; MAO, Shuli; LI, Yongfeng; WO2011/160020; (2011); A2;,
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. 1117-71-1, name is Methyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7BrO2

The (E) -4- bromo crotonate 6g (33.5mmol) was dissolved in THF (60ml) cooled to to 0 ,Under the protection of N2 was added dropwise lithium hydroxide monohydrate 1.83g (43.6mmol) in water(20mL). After the dropping 15min, 0 kept stirred 3h. And then cold water 150ml200ml of petroleum ether was added to the system to continue stirring 10min at 0 . Separating the aqueous phase, at 0 PH adjusted with concentrated hydrochloric acid to 1, with dichloromethane (80mlx3) and extracted. The combined organicPhase was dried over anhydrous sodium sulfate and concentrated to give compound X, a yellow solid 4.5g, 82% yield.In the E-4- mixed with X-bromo crotonic acid and a drop of DMF in DCM (3ml) was added dropwise a solution of oxalylChlorine (0.025g, 1.96mmol). After the dropwise addition, stirring was raised to room temperature for 1h. Completion of the reaction,The solvent was concentrated to afford the intermediate (E) -4- bromo-2-enoyl chloride III, without further treatment,It was used directly in the next reaction.

According to the analysis of related databases, 1117-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Zepletech Biological Pharmaceutical Co., Ltd.; Wang, Kangmin; Chen, Wei; Zhao, Gang; Liu, Jifeng; Pu, Lin; (22 pag.)CN105669521; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics