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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7BrO2

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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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. 868-72-4, name is Dimethyl 2,5-dibromohexanedioate, A new synthetic method of this compound is introduced below., Application In Synthesis of Dimethyl 2,5-dibromohexanedioate

To a solution of dimethyl 2,5-dibromohexanedioate (SM-1) (100 g, 0.301 mol) in toluene and water (400 mL, 3:1) were added K2CO3 (49.88 g, 0.361 mol) and benzylamine (32.23 g, 0.301 mol). The reaction mixture was heated to 80 C under nitrogen atmosphere and stirred for 16 h. After completion of the reaction, the reaction mixture was cooled to room temperature and added EtOAc (200 mL). After stirring for 10 minutes, the organic layer was separated and washed with brine. The organic layer was dried over anhydrous Na SCL and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 20% EtOAc/n-hexane to afford meso compound 1 (48 g, 57%) as a brown thick liquid along with 13 g of racemic compound. (0311) 7.19 (m, 5H), 3.83 (s, 2H), 3.48 (s, 6H), 3.42-3.36 (m, 2H), 2.09-1.98 (m, 2H), 1.94-1.83 (m, 2H). (0312) LCMS (ESI): m/z 277.9 [M++l]

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; APTINYX INC.; KHAN, M., Amin; (110 pag.)WO2019/152681; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 106614-28-2,Some common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Methyl 2,4-difluorobenzoate (1.00 g; 5.81 mmol), 4-fluorophenol (0.72 g; 6.39 mmol) and potassium carbonate (1.61 g; 11.62 mmol) in DMF (20 mL) are stirred at 90C for 4 hours. The reaction mixture is diluted with water and extracted three times with DCM. The combined organic layers are dried over MgSC , filtered and concentrated under reduced pressure. The residue is purified by RP-HPLC (ACN/water + TFA). Yield: 0.45 g (29%) ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1.15 min (method 1)

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
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Electric Literature of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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-(3-Fluorophenyl)acetohydrazide (2.90 g, 17.22 mmol) and ethyl 2-ethoxy-2- iminoacetate (2.5 g, 17.22 mmol) in ethanol (30 mL) was stirred under nitrogen at rt overnight. The resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound ethyl 2-amino-2-(2-(2-(3- fluorophenyl)acetyl)hydrazono)acetate (3 g, 11.23 mmol, 65.2 % yield), which was used without further purification. MS (m/z) 268 (M+H+).

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JEONG, Jae U.; KANG, Jianxing; LEISTER, Lara Kathryn; ROMANO, Joseph J.; (82 pag.)WO2018/7973; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 33842-16-9, 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. 33842-16-9 name is Methyl benzo[d][1,3]dioxole-4-carboxylate, 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.

Method C; BenzoH ,31dioxole-4-carboxylic acidhydrazide (Intermediate compound); A mixture of 1 ,3-benzimidazole-4-carboxylic acid (3.0 g, 17,5 mmol), sulfuric acid (0.17 g, 1.75 mmol) and methanol (40 ml) was stirred at reflux for 15 h. The mixture of the intermediate benzo[1 ,3]dioxole-4-carboxylic acid methyl ester was allowed to reach room-temperature. Hydrazine monohydrate (8.5 g, 175 mmol) was added and the mixture was stirred at reflux for 15 h. The mixture was evaporated, water was added and the crystalline product was isolated by filtration. Yield 2.15 g (68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl benzo[d][1,3]dioxole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NeuroSearch A/S; PETERS, Dan; TIMMERMANN, Daniel, B.; NIELSEN, Elsebet, ?stergaard; DYHRING, Tino; CHRISTENSEN, Jeppe, Kejser; WO2010/86278; (2010); 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 23062-51-3 as follows. Quality Control of Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate

Intermediate A51E: Methyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate To a suspension of aluminum trichloride (809 mg, 6.07 mmol) in benzene (4 mL, 1.214 mmol) at -10 C. was added a solution of Intermediate A51D (300 mg, 1.214 mmol) in benzene (2 mL) under nitrogen. The reaction mixture was gradually warmed up to RT and stirred overnight. It was carefully poured into ice water, extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51E (250 mg, 84%) as a tan solid, which was used for the next step without further purification. MS(ES): m/z=245 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 7.42-7.29 (m, 4H), 7.29-7.16 (m, 1H), 3.77-3.65 (s, 3H), 2.07-1.80 (m, 1H).

According to the analysis of related databases, 23062-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Ester – an overview | ScienceDirect Topics

Related Products of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-isopropyl-5-(4-(6-(l,2,3,6-tetrahydropyridin-4- yl)benzo[d]thiazol-2-yloxy)piperidin-l-yl)-l,2,4-oxadiazole (Compound 43E, 95 mg, 0.223 mmol) and triethylamine (0.08 mL, 0.56 mmol) in CH2C12 (2mL) at 0 C was added methyl 3-(chlorosulfonyl)propanoate (62.5 mg, 0.335 mmol). The reaction mixture was stirred at 0 C for 15 min, then at rt overnight. The reaction mixture was quenched with sat. aq. aHC03 (2 mL) and extracted with CH2CI2 (3 x 3 mL). The combined organic layers were dried ( a2S04), filtered, and concentrated. The residue was purified by column chromatography (silica gel, CH2Cl2-EtOAc gradient 0 to 60% EtOAc) to afford methyl 3-(4-(2-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4- yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-l(2H)-ylsulfonyl)propanoate (75 mg, 0.13 mmol, 58% yield) as an off white solid. LCMS (m/z) =576 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-(chlorosulfonyl)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 541-16-2, 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. 541-16-2, name is Di-tert-Butyl malonate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled(0 C) solution of NaH (60% in mineral oil, 2.2 eq.) in DMF (1.0 M) was slowly added di-t-butylmalonate (1.1 eq.). After 15 min, 2-fluoronitrobenzene derivative (5.00 g) was added to the reactionmixture dropwise at 0 C. The resultant mixture was stirred at room temperature overnight and quenchedwith 0.1 N HCl aq. The resultant aqueous phase was extracted with EtOAc/n-hexane = 1/1. The combinedorganic phases were washed with brine. The resultant organic phase was dried over Na2SO4, filtered, andthe filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography(n-hexane/EtOAc = 100/0 – 30/70).

The chemical industry reduces the impact on the environment during synthesis Di-tert-Butyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yamai, Yu-Suke; Tanaka, Akio; Yajima, Tatsuo; Ishida, Kyoji; Natsutani, Itaru; Uesato, Shinichi; Nagaoka, Yasuo; Sumiyoshi, Takaaki; Heterocycles; vol. 97; 1; (2018); p. 192 – 210;,
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Ester – an overview | ScienceDirect Topics

Related Products of 24807-40-7,Some common heterocyclic compound, 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, molecular formula is C17H18O3, 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.

Methyl 2-((4-((phenylmethyl)oxy)phenyl)methyl)butanoate(32.1).; To a solution of lithium diisopropylamide (6.5 mL, 2.0 M in heptane/THF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (1OmL) and 1,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then iodoethane (1.0 mL, 13 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL), and the mixture was concentrated in vacuo. The residue was disolved in EtOAc (100 mL), washed with brine (2×25 mL), and dried with Na2SO4. The residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15) to give the title compound 32.1. MS ESI (pos.) m/e: 299.0 (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 3-(4-(benzyloxy)phenyl)propanoate, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/130514; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 61367-07-5, These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate 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.

Example 19(1r,4R)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide Step 1. Preparation of (1r,4r)-methyl 4-(4-chloro-3-nitrophenylsulfonamido)cyclo hexanecarboxylate; (1r,4r)-methyl 4-aminocyclohexanecarboxylate HCl salt (7.75 g, 40 mmol) was suspended in a mixture of DCM (50 mL) and then treated with triethylamine (22.31 mL, 160 mmol), followed by 4-chloro-3-nitrobenzene-1-sulfonyl chloride (11.27 g, 44 mmol). The reaction mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aq. HCl (3¡Á100 mL), brine (100 mL) and dried over sodium sulfate. Filtration and concentration of the organic solution gave product (14.1 g) as a yellow solid (MS: (M+H)+=377.3).

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; US2012/28969; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics