Category: esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Computed Properties of C7H13BrO2

To the mixture of the A-4 (1500 mg, 5.08 mmol) and K2C03 (1402.39 mg, 10.16 mmol) in MeCN (5 mL) was added tert-butyl 3-bromopropanoate (1062.36 mg, 5.08 mmol), and the mixture was stirred at 50 C for 16 hours. The mixture was cooled to r.t, diluted with sat.NH4Cl (50 mL), extracted with EtOAc (50 mL x 2), and the combined phase was washed over brine (20 mL), dried over Na2S04 and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 5% to 10% to 20%) to afford A-24 (1300 mg, 3.07 mmol) as an oil. 1H NMR (DMSO-d6 400MHz) deltaH = 7.83 (d, 2H), 7.72 (s, 1H), 7.47 (d, 2H), 7.43 (s, 2H), 4.10 (t, 2H), 2.75 (t, 2H), 1.31 (s, 9H).

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, tert-Butyl 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 581065-95-4, A common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, molecular formula is C15H31NO6, 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.

To a solution of compound 23-3 (33mg, 0.102 mmol), compound 12-7 (40 mg, 0.051 mmol) and 54 mu^ of diisopropylethylamine in 1 mL of DMF was added 38 mg of HATU. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was purified by HPLC to give 52 mg of compound 23-4. MS (ESI) m/z 525[M+2H], 1049[M+H].

The synthetic route of 581065-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBRX, INC.; MIAO, Zhenwei; ATKINSON, Kyle, C.; BIROC, Sandra; BUSS, Timothy; COOK, Melissa; KRAYNOV, Vadim; MARSDEN, Robin; PINKSTAFF, Jason; SKIDMORE, Lillian; SUN, Ying; SZYDLIK, Angieszka; VALENTA, Ianina; WO2012/166560; (2012); 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-amino-4,5-dimethoxybenzoate

Step 1a. 6,7-Dimethoxyquinazolin-4(3H)-one (Compound 0102) A mixture of methyl 2-amino-4,5-dimethoxybenzoic acid 0101 (2.1 g, 10 mmol), ammonium formate (0.63 g, 10 mmol) and formamide (7 ml) was stirred and heated to 190~200 C. for 2 hours. Then the mixture was cooled to room temperature. The precipitate was isolated, washed with water and dried to provide the title compound 0102 as a brown solid (1.8 g, 84.7%): LCMS: m/z 207 [M+1]+; 1H-NMR (DMSO.) delta 3.87 (s, 3H), 3.89 (s, 3H), 7.12 (s, 1H), 7.43 (s, 1H), 7.97 (s, 1H), 12.08 (bs, 1H).

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2009/76022; (2009); A1;,
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. 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17205-02-6

3-hydroxy-cyclobutane-carboxylic acid ethyl (800 mg)In tetrahydrofuran (25mL) solution,Synthesized in Reference Example 2-53 (1) 2-chloro-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.24 g),Triphenylphosphine (5.68g),Toluene solution of diethyl azodicarboxylate (2.2M, 9.84mL) was added,It was stirred at room temperature for 13 hours. The temperature was raised to 60 , and the mixture was stirred for 7 hours at the same temperature.The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) in the purified twice, to give the title compound (2.22g) as a colorless solid .

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 17205-02-6.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 502764-52-5, 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. 502764-52-5 name is Diethyl dithieno[3,2-b:2′,3′-d]thiophene-2,6-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.

152.0 g (0.446 mol) of the compound represented by the formula 3-c obtained from the above reaction formula 17 and 2.3 L of tetrahydrofuran were added to a 5 L round bottom flask, and then 95.5 g (2,277 mol) of lithium hydroxide was dissolved in 2.3 L of water, The reaction mixture was stirred for 30 minutes and then refluxed for 6 hours. After the temperature was lowered to room temperature, 3 L of 1 N hydrochloric acid was poured, and the solid was filtered, washed with methanol and dried to obtain 112.0 g (88.2%) of the compound represented by the formula 3-d.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl dithieno[3,2-b:2′,3′-d]thiophene-2,6-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SFC Ltd.; Che Jong-tae; Jeong Seong-uk; Park Seok-bae; Kang Yeong-jin; Ryu Yeon-gwon; (45 pag.)KR101791161; (2017); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 14062-24-9, 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. 14062-24-9, name is Ethyl 4-chlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 2-(alpha-ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine Add (drop by drop at 90 in a stream of nitrogen to let the alcohol escape) a solution of 4.6 g of sodium in 100 ml of ethyl alcohol to a mixture of 53.2 g of the title compound of Example 1 and 29.8 g of ethyl 4-chlorophenylacetate. Stir it for a further 4 hours at 90 and then cool it to ambient temperature. Mix the cooled reaction mixture with 100 ml of water and 100 ml of diethyl ether, collect the organic phase and dry the latter over sodium sulfate. Concentrate the dried organic phase and then distil off any excess ethyl 4-chlorophenylacetate under a high vacuum to obtain a crude yield [15.5 g (34% of theory)] of the title compound as yellow oil.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-chlorophenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US4221788; (1980); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 20921-00-0, 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 20921-00-0 as follows.

To a mixture of compound 6B (3.41 g, 14.956mmol) in THF at 0 was added CH3MgBr (32.9 mmol) . The mixture was allowed to stir at 020 for 16 hours, and then the mixture was quenched with NH4Cl, and extracted with ethyl acetate. The organic extract was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. Tthe residue obtained was purified using flash column chromatography (petroleum ether: ethyl acetate 20: 15: 1) to provide compound 6C.

According to the analysis of related databases, 20921-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YU, Wensheng; KOZLOWSKI, Joseph A.; TONG, Ling; COBURN, Craig A.; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; (101 pag.)WO2018/32467; (2018); 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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (10 g) obtained in Reference Example 2(1), 1,4-diiodobutane (19.2 g) and sodium carbonate (16.4 g) are suspended in a mixture of tetrahydrofuran (300 ml) and N,N-dimethyl acetamide (60 ml), and the mixture is stirred at 70C for 20 hours. The reaction solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane = 1/5) to give methyl trans-4-pyrrolidin-1-ylcyclohexanecarboxylate (10.9 g). APCI-MS M/Z:212[M+H]+.

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

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 651734-58-6, These common heterocyclic compound, 651734-58-6, name is Methyl 2-fluoro-3,5-dimethoxybenzoate, 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.

Solution of 2-fluoro-3,5-dimethoxy-benzoic acid methyl ester (8.3 g, 38.7 mmol) in 330 mL of acetonitrile is cooled to O0C. Under nitrogen atmosphere SO2Cl2 (5.2 g, 38.7 mmol) is added dropwise. The reaction mixture is warmed to room temperature slowly. After 1 hour, the reaction is completed. The reaction is quenched with saturated sodium bicarbonate, and extracted with EtOAc three times. The organic layer is washed with brine, dried with MgSO4 and concentrated. The crude mixture is separated by silica gel column chromatography eluting with a gradient of hexane/ether (20:1 to 10:1 and 5:1) to obtain 2- chloro-6-fluoro-3,5-dimethoxy-benzoic acid methyl ester (20); 1H NMR 400 MHz(CDCl3) delta 6.64 (d, IH), 3.97 (s, 3H), 3.91 (s, 3H), 3.89 (s, 3H);MS m/z 249.0 (M + 1).

The synthetic route of 651734-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/8747; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15568-85-1, 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. 15568-85-1 name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

1 eq of 3-bromo-2-methoxy-4-aminopyridine was dissolved in isopropanol, then 2 eq of compound 49 was added thereto. After heating to 110 C., the mixture was allowed to react for 1 h with stirring, and then a large amount of solid was precipitated. 2 h later, the solid was cooled to room temperature, washed with isopropanol and ether to give the product compound 57, yield 92%; The compound obtained above was suspended in diphenyl ether at 10 ml/g, and the mixture was heated to 220 C. and allowed to react for 1 h with stirring, and then a large amount of solid was precipitated, which was cooled to room temperature, washed with a large amount of petroleum ether and filtered to give the compound 58, yield 96%. The above solid was dissolved in methanol, and 2 eq of ammonium formate was added therein followed by the addition of 10 wt % of 10% Pd/C. The mixture was allowed to react with stirring at 60 C. and the reaction was monitored by TLC. After the reaction was completed, the resultant was cooled and filtered, the filtrate was concentrated and then extracted with EA, washed with saturated NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the compound 59. 1H NMR (400 MHz, DMSO) delta 8.89 (s, 1H), 8.46 (s, 1H), 7.87 (d, J=7.6 Hz, 1H), 6.75 (s, 1H), 5.97 (d, J=7.6 Hz, 1H), 3.91 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; LONG, Yaqiu; GENG, Meiyu; XU, Zhongliang; AI, Jing; (100 pag.)US2018/244667; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics