Tag: M.W=300-400

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

107 mg (0.335 mmol) of tert-Butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate and 93 mg (0.369 mmol) of (2,5-dioxopyrrolidin-1-yl) 2-(2,5-dioxopyrrol-1-yl)acetate were dissolved in 5 ml of dimethylformamide, and 0.074 ml (0.671 mmol) of N-methylmorpholine were added. The reaction mixture was stirred at RT overnight. 0.048 ml (0.838 mmol) of acetic acid were added and the reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 125*30; 10mu, flow rate: 50 ml/min, MeCN/water/0.1% TFA). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 133 mg (86%, purity 100%) of tert-Butyl 3-[2-[2-[2-[2-[[2-(2,5-dioxopyrrol-1-yl)acetyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate. LC-MS (Method 1): Rt=0.82 min; MS (ESIpos): m/z=459 (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 581065-95-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; WITTROCK, Sven; BERNDT, Sandra; GRITZAN, Uwe; FITTING, Jenny; STELTE-LUDWIG, Beatrix; JONES, Patrick; MAHLERT, Christoph; VOTSMEIER, Christian; SCHOeNFELD, Dorian; TRAUTWEIN, Mark; WEBER, Ernst; PAWLOWSKI, Nikolaus; GREVEN, Simone; GLUeCK, Julian Marius; HAMMER, Stefanie; DIETZ, Lisa; MAeRSCH, Stephan; (357 pag.)US2020/138970; (2020); A1;,
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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 153559-48-9 as follows. Product Details of 153559-48-9

Example 3: Preparation of bexaroteneTo suspension of methyl 4-[l-(5,6,7,8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthalenyl)-l- ethenyljbenzoate (100 g) in methanol (1000 ml), 5N aqueous potassium hydroxide (170 ml) was added at 25-30C and the reaction mixture was refluxed for 8 hours. After completion of reaction (monitored by HPLC), reaction mass was cooled to 35-40 C and washed with 50% ethyl acetate: n-heptane mixture (2 x 500 ml). The organic layer was discarded and the aqueous layer was cooled to 10-15 C. Thereafter pH of aqueous layer was adjusted to 1-2 by addition of concentrated hydrochloric acid (100 ml). The resulting mixture was then stirred at 20-25C, stirred for 1 hour and precipitated solid was filtered. The resulting solid was slurry washed with demineralized water (100 ml), centrifuged and dried to give 84.6 g of title compound having purity 98.89 %, none of the impurities C, D, E, F were detected by HPLC

According to the analysis of related databases, 153559-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; BHIRUD, Shekhar, Bhaskar; SARIN, Gurdeep, Singh; SHARMA, Bimal, Kumar; GERA, Pardeep; WO2011/141928; (2011); A1;,
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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 764667-64-3 as follows. HPLC of Formula: C14H11F3O5

Under nitrogen protection,Acetonitrile (284 mL) was added to a 250 mL three-necked flask in sequence,Compound C (56.7 g, 0.179 mol) and benzyl alcohol (19.4 g, 0.179 mol),Stirring.Heating to reflux(The internal temperature of 80 ~ 84 for the normal boiling point)About 24 hours.Cooling to below 30 ,concentrate,3 V methanol was added,0 ~ 5 crystallization of 12h,Filtered product 47.2g,Yield 81.6%.

According to the analysis of related databases, 764667-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai SynCores Technologies, Inc.; Qian, Wangke; Hong, Jian; Wang, Yusheng; Wang, Boyu; Huang, Luning; Gu, Hong; (8 pag.)CN105566138; (2016); A;,
Ester – Wikipedia,
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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;,
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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 72338-48-8 as follows. category: esters-buliding-blocks

2.98 g of amantadine was dissolved in 15 mL of DMF, and 5.5 g of ethyl bromododecanoate and 4.9 g of K2CO3 were added.Reaction at 60 C for 16 hours;Then diluted with 100 mL of water and extracted with ethyl acetate (3¡Á50 mL);After the organic phase is combined, it is dried with sodium, and then the solid is filtered off.The filtrate is concentrated in vacuo and purified to give a yellow oil, 12-(adamantyl)aminododecanoate;

According to the analysis of related databases, 72338-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Agricultural University; Wang Zhanhui; Jiang Haiyang; Wen Kai; Shen Jianzhong; Zhang Xiya; Chen Chaochao; Duan Changfei; Yu Wenbo; Yu Xuezhi; (17 pag.)CN110105232; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, A new synthetic method of this compound is introduced below.

118 mg (566 mumol) of N-[(benzyloxy)carbonyl]glycine were initially charged in 5.0 ml of DMF, 200 mg (622 mumol) of tert-butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 130 mg (849 mumol) of 1-hydroxy-1H-benzotriazole hydrate and 130 mg (679 mumol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added and the mixture was stirred at RT for 1 h. Ethyl acetate was added and the mixture was extracted twice with 5% citric acid solution and with saturated sodium hydrogencarbonate solution. The organic phase was washed twice with saturated sodium chloride solution and dried over magnesium sulphate. The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 274 mg (95% of theory) of tert-butyl 1-({N-[(benzyloxy)carbonyl]glycyl}amino)-3,6,9,12-tetraoxapentadecan-15-oate. LC-MS (Method 12): Rt=1.69 min; MS (ESIpos): m/z=513 (M+H)+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; MARX, Leo; JOHANNES, Sarah Anna Liesa; STELTE-LUDWIG, Beatrix; DIETZ, Lisa; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (481 pag.)US2019/77752; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

868-72-4,Some common heterocyclic compound, 868-72-4, name is Dimethyl 2,5-dibromohexanedioate, molecular formula is C8H12Br2O4, 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 stirring solution of dimethyl 2,5-dibromohexanedioate (SM) (50 g, 0.15 mol) in toluene:water (150 mL, 2: 1) were added benzyl amine (16 mL, 0.15 mol) and K2CO3 (24 g, 0.18 mol) at room temperature. The reaction mixture was heated to reflux at 110 C and stirred for 4 h. After consumption of the starting material (by TLC), reaction mixture was cooled to room temperature and extracted with diethyl ether (2 x 50 mL). Separated organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain compound 1- mixture (39 g, 93%) as liquid. This material was purified by silica gel column chromatography eluting with 20% EtOAc/n-hexane to afford compound 1-Fl (10 g), compound 1-F2 (13 g) and compound 1-Fl and F2 as a mixture (16 g) as liquid. H NMR (500MHz, CDC13): delta 7.32-7.17 (m, 5H), 3.89 (s, 2H), 3.55 (s, 6H), 3.45-3.38 (m, 2H), 2.08- 1.99 (m, 4H). LCMS (m/z): 278.2 [M++l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2,5-dibromohexanedioate, its application will become more common.

Reference:
Patent; APTINYX INC.; KHAN, Amin, M.; (197 pag.)WO2018/26792; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 764667-64-3, name is 5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C14H11F3O5, 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. 764667-64-3.

2,4, 5-TRIFLUOROPHENYLACETIC acid (2-1) (150 g, 0.789 mol), Meldrum’s acid (125 g, 0. 868 mol), and 4- (DIMETHYLAMINO) pyridine (DMAP) (7.7 g, 0063 mol) were charged into a 5 L three-neck flask. N, N-DIMETHYLACETAMIDE (DMAC) (525 ML) was added in one portion at room temperature to dissolve the solids. N, N-diisopropylethylamine (282 ML, 1.62 mol) was added in one portion at room temperature while maintaining the temperature below 40 C. Pivaloyl chloride (107 ML, 0.868 mol) was added dropwise over 1 to 2 h while maintaining the temperature between 0 and 5 C. The reaction mixture was aged at 5 C for 1 h. Triazole hydrochloride 1-4 (180 g, 0.789 mol) was added in one portion at 40-50 C. The reaction solution was aged at 70 C for several h. 5% Aqueous sodium hydrogencarbonate solution (625 ML) was then added dropwise at 20-45 C. The batch was seeded and aged at 20-30 C for 1-2 h. Then an additional 525 mL of 5% aqueous sodium hydrogencarbonate solution was added dropwise over 2-3 h. After aging several h at room temperature, the slurry was cooled to 0-5 C and aged 1 h before filtering the solid. The wet cake was displacement-washed with 20% aqueous DMAC (300 mL), followed by an additional two batches of 20% aqueous DMAC (400 mL), and finally water (400 mL). The cake was suction-dried at room temperature. The isolated yield of final product 2-3 was 89%.

The synthetic route of 5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/20920; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18013-97-3, name is Diethyl 2,5-dibromoterephthalate, 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. 18013-97-3

In a 100 mL Schlenck tube, tin hydride material a1′ (4.7 g) and brominated material b1′ (2.8 g) were successively added.Pd(PPh3)4 (890 mg), toluene (50 mL),Under nitrogen protection, heated under reflux for 40 hours,After removing the toluene by vacuum evaporation and passing through the silica gel column,Dichloromethane as eluent gave the product c1′ (2.5 g, yield 74%) as a yellow solid.

Statistics shows that 18013-97-3 is playing an increasingly important role. we look forward to future research findings about Diethyl 2,5-dibromoterephthalate.

Reference:
Patent; (31 pag.)CN107652304; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

868-72-4, A common compound: 868-72-4, name is Dimethyl 2,5-dibromohexanedioate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Dimethyl 2,5-dibromoadipate (437 g) was added to DMF (4 L).Then, cesium carbonate (1 Kg) was slowly added thereto and heated to 120 C, and stirred for 36 hours.After the reaction is over, cool,Pour the reaction solution into 2L of ice water.Extraction with ethyl acetate (800 ml X3).The extracts were also combined, washed, dried and concentrated to give a crude material.Further recrystallization from n-hexane to obtainDimethyl 1,2-cyclobutanedicarboxylate(94g, yield 42%),

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, Dimethyl 2,5-dibromohexanedioate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Kaipu Chemical Co., Ltd.; Tan Xianghui; Luo Linfeng; Sun Yanping; Jia Junjian; Zhou Chen; (6 pag.)CN108658762; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics