Author: Jessica.F

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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Quality Control of Chloromethyl ethyl carbonate

Example 59: 4-{(R)-3-[Bis-(ethoxycarbonyloxymethoxy)-phosphoryl]-2-[(2-pheiiyl- thiazole^-carbony^-aminoj-propionylj-piperaziiie-l-carboxylic acid butyl ester A solution of Example 9 (100 mg) and NEt3 (0.08 mL) in DMPU (0.35 mL) was stirred for 10 min at RT. Then, NaI (35 mg) and carbonic acid chloromethyl ester ethyl ester (0.76 mg, prepared as described in WO2004092189) were added. The mixture was stirred overnight at 500C under argon. The reaction mixture was washed with H2O and the aq. phase extracted with toluene (3x). The combined org. phases were dried over Na2Stheta4 and concentrated to dryness. CC purification (EA/[CH2Cl2/Me0H 8:2] 1:0 to 3:1) gave 55 mg of the desired product. LC-MS: tR = 1.07 min; [M+H]+: 729.28.

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; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; HILPERT, Kurt; HUBLER, Francis; LEHMANN, David; MEYER, Emmanuel; RENNEBERG, Dorte; WO2010/122504; (2010); A1;,
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Application of 34837-84-8, 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. 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5A. methyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate. A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 ML), at -78 °C, was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 ML, 14 mmol).. After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 ML) was added in portions.. The reaction mixture was stirred for 60 minutes at -78 °C and at 0 to 5 °C for 12 hours.. The mixture was quenched with 10percent citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69percent). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J = 9 Hz, 2H), 8.25 (d, J = 9 Hz, 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, Methyl 2-(4-fluorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; EP1206474; (2004); B1;,
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Application of 18927-05-4, These common heterocyclic compound, 18927-05-4, name is Methyl 3-Methoxyphenylacetate, 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.

General procedure: 1.4mmol of 5-amino-1-substituted-4-carboxamide-1H-imidazole (1) was dissolved in 10mL of absolute methanol. Then 5.6mmol of the appropriate ester isadded into this solution. This mixture was added in 10mL ofmethoxide-methanol solution prepared from sodium (0.15 g, 6.3mmol) and 10mL of absolute methanol. The mixture was refluxed for 15-20 h. After cooling, the solvent was evaporated off and the residue was taken into ethyl acetate. The organic phase was dried over Na2SO4 and evaporated. And the residue was purified via silica gel chromatography(eluent: the mixture of ethyl acetate and methanol) to obtainthe pure product (2a-2q).

Statistics shows that Methyl 3-Methoxyphenylacetate is playing an increasingly important role. we look forward to future research findings about 18927-05-4.

Reference:
Article; Yuan, Wei; Zhao, Xin-Yun; Chen, Xi; Zhan, Chang-Guo; Journal of Chemistry; vol. 2016; (2016);,
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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. 3469-00-9, name is Methyl Diphenylacetate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl Diphenylacetate

(2) Preparation of 2,2-diphenylethanol To a 500mL three-opening flask was slowly added a solution of diisobutylaluminum hydride in toluene (282mL, 1mol/L) at -30C. After stirring, to the resulting mixture was slowly added a solution of methyl 2,2-diphenylacetate (21g, 92.8mmol) in dichloromethane dropwisely. After the completion of dropwise addition, the reaction was conducted at 25 C for 12 hours. After the completion of reaction monitored by TLC, to the resulting mixture was slowly added methanol (10mL), dichloromethane (100mL) and an aqueous sodium hydroxide solution (100mL, 1mol/L) at -20C. After the completion of reaction, to the reaction solution was added dichloromethane for extraction. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce 2,2-diphenyl ethanol (17 g) in a yield of 92.4 %.

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 3469-00-9.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
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Application of 99974-66-0, 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. 99974-66-0 name is Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate, 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.

a) Diethyl 3-[(methylsulfonyl)oxy]-1,1-cyclobutanedicarboxylate A solution of diethyl 3-hydroxy-1,1-cyclobutanedicarboxylate (0.268 g, 0.00116 mol) in pyridine (7 mL) was cooled to 0 C. Methanesulfonyl chloride (0.11 mL, 0.160 g, 0.00140 mol) was added dropwise, keeping the temperature below 2 C. The mixture was stirred for four hours, and then poured into ice water (20 mL) and extracted with ethyl ether (2*10 mL). The combined organic layers were washed with water (3*10 mL) and brine (10 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give diethyl 3-[(methylsulfonyl)oxy]-1,1-cyclobutanedicarboxylate (0.302 g, 0.00102 mol) as a yellow oil.: 1H NMR (CDCl3, 400 MHz) 5.08-5.11 (m, 1H), 4.23 (q, 4H), 3.01 (s, 3H), 2.98-3.03 (m, 2H), 2.81-2.86 (m, 2H), 1.27 (t, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
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These common heterocyclic compound, 13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, 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. category: esters-buliding-blocks

To 3- methylamino-but-2-enoic acid methyl ester (5.Og, 39.1mmol) in THF (7OmL) was added pyridine (3.7mL). The mixture was cooled to O0C, and 4-bromobenzoyl chloride (8.55g, 39.1mmol) in THF (3OmL) was added dropwise over 2 minutes. The reaction was warmed to room temperature over 1 hour and then stirred at room temperature overnight. Aqueous work-up gave the title compound.

The synthetic route of Methyl 3-(methylamino)but-2-enoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; HUTCHINSON, John Howard; SEIDERS, Thomas Jon; WANG, Bowei; ARRUDA, Jeannie M.; ROPPE, Jeffrey Roger; PARR, Timothy; WO2010/141761; (2010); A2;,
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Synthetic Route of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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.

Step 30c: Methyl 4-(N-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-yl)sulfa- moyl)benzoate (Compound 1404)A mixture of 0108 (0.27 g, 1 mmol), 1403 (0.23 g, 1 mol) in pyridine (10 ml) was stirred at 0C for 3 h. Water was added to afford the crude product. The crude product was purified by flash column chromatography (EtOAc: petroleum ether = 1 : 10) to afford the pure product 1404 (0.35 g, 76 %): LCMS: 468 [M+l]+. 1H NMR (400MHz, DMSO-d6) delta 1.16 (s, 9H), 3.88 (s, 3H), 4.13 (s, 2H), 6.94 (s, IH), 7.91 (d, J= 5.1 Hz, 2H), 8.12 (d, J= 5.1 Hz, 2H), 12.06 (s, IH).

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURIS, INC.; WO2009/36016; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18358-63-9,Some common heterocyclic compound, 18358-63-9, name is Methyl 4-(methylamino)benzoate, 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.

Part D: To the mixture of the product from Step C (412.0 mg, 2.5 mmol) and Et3N (0.5 mL) in CH2Cl2 at 0 C. was added chloroacetyl chloride (0.24 mL, 3.0 mmol) and DMAP (15 mg). After stirring at this temperature for 1.5 hr, the reaction mixture was washed with water and brine and dried over MgSO4. The residue was purified by chromatography on silica gel (20% ethyl acetate in hexane) to give the desired product as a white solid. LC/MS ESI found: (M+1)+=242.3.

The synthetic route of 18358-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Han, Wei; Hu, Zilun; Qiao, Jennifer; US2003/232804; (2003); A1;,
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Electric Literature of 680-65-9,Some common heterocyclic compound, 680-65-9, name is Diethyl difluoromalonate, molecular formula is C7H10F2O4, 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.

In a dry 25 mL round bottom flask under an Ar atmosphere, NaOEt (9.71 mL, 26.0mmol) in EtOH (21 % weight) and diethyl-2,2-difluoromalonate (2.55 g, 13.0 mmol) werestirred at rt for 10 mm. A solution of Example id (554 mg, 1.30 mmol) in EtOH (6.00mL) was added dropwise and the reaction was stirred at rt over 18 hrs. The EtOH wasremoved in vacuo and the crude oil was dissolved in 1 M HC1 (10 mL). The aqueoussolution was extracted with EtOAc (20 mL x 3), and the combined organics were washedwith aq NaC1 (20 mL), dried over Na2SO4, filtered into a round bottom flask andconcentrated in vacuo to give the title compound as a crude brown oil (749 mg, 1.30mmol). MS (ESI) 576.0 [M+H]+.

The synthetic route of 680-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; BUSCH, Brett, B.; AVERBUJ, Claudia; VALENTE, Meriah; WURTZ, Nicholas; RAO, Prasanna Savanor, Maddu; SHETTY, Jeevanprakash; VENU, Alla; WO2014/152738; (2014); A1;,
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Synthetic Route of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

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-amino-4-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics