Category: esters-buliding-blocks

Some common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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. Product Details of 252881-74-6

[3918] 150 mg (541 flillOl) oftert-butyl3-{2-[2-(2-aminoethoxyl)ethoxy ]ethoxy }propanoate were dissolved in 3 ml ofdichloromethane, 1.5 ml of trifluoroacetic acid were added,and the reaction mixture was stirred at RT for 1 h, thenconcentrated. 181 mg ( 100% of theory) of the title compoundwere obtained.[3919] MS (EI): m/z 222 (M+Ht

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 252881-74-6, its application will become more common.

Reference:
Patent; SEATTLE GENETICS, INC.; LERCHEN, Hans-Georg; LINDEN, Lars; SHEIKH, Sherif El; WILLUDA, Joerg; KOPITZ, Charlotte C.; SCHUHMACHER, Joachim; GREVEN, Simone; MAHLERT, Christoph; STELTE-LUDWIG, Beatrix; GOLFIER, Sven; BEIER, Rudolf; HEISLER, Iring; HARRENGA, Axel; THIERAUCH, Karl-Heinz; BRUDER, Sandra; PETRUL, Heike; JOeRISSEN, Hannah; BORKOWSKI, Sandra; US2015/246136; (2015); A1;,
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Related Products of 63485-50-7, These common heterocyclic compound, 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, 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.

8-0I (Intermediate 126A) (380 mg, 2.23 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and methyl 3-hydroxycyclobutanecarboxylate (0.37 mL, 3.5 mmol) was added, followed by DIAD (0.68 mL, 3.5 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-1 00% EtOAc-hexanes gradient to give a mixture of cis and trans isomers which were separated on an IC 30 X 250 mm column eluting with 50% EtOH in hexanes to give the title compound (137 mg, 21 %). 1H NMR (400 MHz, CD3SOCD3) delta 2.48- 2.59 (m, 2 H), 2.82 (ddd, J = 14, 7, 5 Hz, 2 H), 3.22-3.32 (m, 1 H), 3.31 (s, 3 H), 5.07 (t, J = 7 Hz, 1 H), 6.91 (dd, J = 1 1 , 3 Hz, 1 H), 7.31 (dd, J = 9, 3 Hz, 1 H), 7.59 (dd, J = 8, 4 Hz, 1 H), 8.30 (dd, J = 8, 2 Hz, 1 H), 8.83 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 276.

Statistics shows that cis-Methyl 3-hydroxycyclobutanecarboxylate is playing an increasingly important role. we look forward to future research findings about 63485-50-7.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Synthetic Route of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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 suspension of ethyl 2-(4-chloro-2-hydroxyphenyl)acetate [CAS 1261826-30-5] (8.5 g, 39.6 mmol), C52CO3 (25.8 g, 79.2 mmol) in DMF (130 mL) at 10C was added dropwise tert-butyl 4-bromobutanoate [CAS 110611-91-1] (7 mL, 39.6 mmol). The mixture was stirred at room temperature overnight. The mixture wasdiluted with EtOAc and water. The layers were separated. The organic layer was washed with water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 90/1 0). The pure fractions were combined and concentrated to dryness to give tert-butyl 4-(5-chloro-2-(2-ethoxy-2-oxoethyl)phenoxy)butanoate 7a (12.7 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-bromobutanoate, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
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Synthetic Route 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.

To a solution of 6-bromo-4-phenyl-3-isocoumarincarboxylic acid methyl ester (3.60 g) in methanol (50 ml) was added 4-aminomethylbenzoic acid methyl ester (3.16 ml) and the mixture was stirred at room temperature for 18 hrs. The solvent was evaporated under reduced pressure and 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in methanol (100 ml). Conc. sulfuric acid (10 ml) was added, and the mixture was heated under reflux for 3 hr. The solvent was evaporated under reduced pressure, water was added under ice-cooling and the mixture was neutralized with potassium carbonate. The solution was extracted with ethyl acetate and the extract was washed with saturated brine. Sodium sulfate was added to dry the mixture. The obtained residue was recrystallized from methanol to give the title compound (3.39 g, 67%).1H-NMR (CDCl3) delta: 3.18 (3H, s), 3.89 (3H, s), 5.45 (2H, s), 7.24-7.47 (8H, m), 7.67 (1H, dd, J=1.8, 8.4 Hz), 7.97 (2H, d, J=8.4 Hz), 8.40 (1H, d, J=8.4 Hz).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1484320; (2004); A1;,
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Reference of 773873-95-3, 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. 773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step b: (2,2-Difluoro-benzo[1,3]dioxol-5-yl)-methanol Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0 C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0 C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 76% over two steps) as a colorless oil.

The synthetic route of Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadida Ruah, Sara S.; Miller, Mark T.; Bear, Brian; McCartney, Jason; Grootenhuis, Peter D. J.; US2008/9524; (2008); A1;,
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Synthetic Route of 555-43-1, A common heterocyclic compound, 555-43-1, name is Propane-1,2,3-triyl tristearate, molecular formula is C57H110O6, 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: An assay mixture consisting of 1 ml of liquid ester or 1 g of solid ester, 3 ml of isopropanol, 5 ml of phosphate buffer (pH=8.0), and 1 ml of the lipase solution was incubated for 15 min at 30C with stirring at 180 rpm. The reaction was terminated by the addition of 95% ethanol, and the amount of liberated fatty acids after incubation was determined by titrating with 50 mM NaOH in the presence of two drops of phenolphthalein solution as the indicator. The control experiment was performed under the same conditions with the addition of 95% ethanol prior to the reaction. One unit of lipase activity was defined as the amount of enzyme required to liberate 1 mumol of free fatty acid per minute under the experimental conditions.

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:
Article; Li, Xiao-Lu; Zhang, Wen-Hui; Wang, Ying-Dong; Dai, Yu-Jie; Zhang, Hui-Tu; Wang, Yue; Wang, Hai-Kuan; Lu, Fu-Ping; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 16 – 24;,
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Adding a certain compound to certain chemical reactions, such as: 134-20-3, name is Methyl 2-aminobenzoate, 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 134-20-3, HPLC of Formula: C8H9NO2

In a 100 L double-layer glass reactor, 26.50 kg of dichloromethane, 8.0 kg of purified water, and 3.02 kg of methyl 2-aminobenzoate were successively added, and the mixture was uniformly stirred.A solution of bromine (3.83 kg) in dichloromethane (5.3 kg) was slowly added to the reaction mixture obtained above at normal temperature.After the addition was completed, stirring was continued for 10 minutes, and 2.50 kg of a 30% hydrogen peroxide solution was slowly added to the reaction solution, and the mixture was stirred for 6 hours, and the reaction was completed.To the reaction solution, slowly add 3.5 kg of a 20% sodium sulfite solution to quench the reaction, phase separate, and extract the organic phase with 8.0 kg of purified water.The aqueous phase was extracted twice with dichloromethane, and the organic phases were combined.The residue was transferred to a 100 L autoclave and 15.0 kg of methanol was added, heated to dissolve, and stirred for 15 minutes.The reaction solution was transferred to a crystallizing tank, and slowly cooled to room temperature at rest, and then placed in a refrigerator and further cooled to 0 C for 2 hours.The solid was filtered and dried at 50 C. After the water was passed, the yield was 5.88 kg, and the yield was 96%.

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Reference:
Patent; Guangzhou Yipinhong Pharmaceutical Co., Ltd.; Guangdong Zerui Pharmaceutical Co., Ltd.; Li Hanxiong; Lan Xiaobing; Yan Xinxing; (20 pag.)CN109535010; (2019); A;,
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Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. Formula: C6H8O2

To a solution of (E)- and/or (Z)-N-hydroxy-3-fluoro-benzenecarboximidoyl chloride (11.1 g, 64 mmol) in diethylether (151 mL) was added ethyl 2-butynoate (7.2 g, 7.5 mL, 64 mmol) at 0 C. followed by the dropwise addition of triethylamine (7.8 g, 10.7 mL, 77 mmol) and the resulting mixture allowed to warm up to room temperature overnight. The mixture was then poured onto ice-water, and extracted with diethylether. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (6.3 g, 39%) which was obtained as a white solid. MS: m/e=250.1 [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 4341-76-8, its application will become more common.

Reference:
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Lucas, Matthew C.; Thomas, Andrew; US2009/143371; (2009); A1;,
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Reference of 2475-80-1, 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 2475-80-1 as follows.

To 2-nitro-5-methoxy-benzoic acid (4 g, 20.3 mmol) in 35 mL of methanol was added trimethylsilyldiazomethane (35 mL, 70 mmol, 2 M in dichloromethane) at RT dropwise. The mixture was stirred at RT for 10 h. To the mixture was added several drops of acetic acid. The resulting solution was concentrated in vacuo to give a brown solid. To this intermediate was added 150 mg of Pd/C (10%). The mixture was stirred under 40 psi of hydrogen gas for 5 h. The mixture was filtered and washed with dichloromethane. The filtrate was concentrated m vacuo to give a dark red oil. To this aniline intermediate were added 30 mL of ethanol and 5 mL of concentrated HCl. To this mixture at 00C was dropwise added a solution of sodium nitrite (5.6 g, 81.2 mmol) in 15 mL of water to form the diaza salt. After 1 h at 00C, to the resulting dark red solution was slowly added sodium azide (8.6 g, 132 mmol) in 15 mL of water. After 1 h at O0C, the slurry was filtered and washed with saturated sodium carbonate solution and water to give the azide as a red solid. The same DIBALH reduction procedure as described above gave the benzyl alcohol as a dark red oil. To this oil in 100 mL of dichloromethane was added PCC (8 g) at O0C. The mixture was stirred at RT for 4 h and purified by Biotage (2-20% ethyl acetate in hexane) to give the aryl azide aldehyde intermediate as a light yellow solid. To a solution of this intermediate (1.1 g, 6.3 mmol), malononit?le (423 mg, 0 40 mL, 6 4 mmol) and 15 mL of dichloromethane was added a solution of pipe?dine (145 mg, 0.17 mL, 1.7 mmol) in 5 mL of dichloromethane. After 2 h at RT, the mixture was filtered and the solid was washed with dichloromethane to give the tricycle as a brown solid. To this intermediate (0.66 g, 2 9 mmol) m 10 mL of DME and 20 mL of dichloromethane was added DIBALH (7.04 mL, 7.04 mmol, 1 M in hexane) at – 780C The mixture was stirred at -780C for 3 days. The mixture was then quenched with water and saturated Rochelle’s salt (200 mL) at -780C. The aqueous layer was then extracted with 30% isopropyl alcohol in chloroform. The combined fractions were dried with sodium sulfate and concentrated in vacuo. The residue was purified by RP-HPLC to give a light yellow solid A similar homologation sequence described in EXAMPLE 86 gave the intermediate enamide. To a slurry of this enamide (18 mg) in 150 mL of methanol was added p-toluenesulfonylhydrazide (400 mg). The mixture was heated at reflux overnight. After removing the solvent, the residue was purified by RP-HPLC to give a pale yellow solid. Following the similar hydrolysis and demethylation procedures as described for the preparation of EXAMPLE 86, the desired compound was obtained as a white solid 1H NMR (CD3OD, 500 MHz) delta 8.50 (1H, d), 8.47 (1H, d), 8.00 (1H, d), 7.84 (1H, s), 7.52 (1H, t), 7.34 (1H, dd), 7.29 (1H, d), 7.11 (1H, t), 3.50 (2H, t), 3.06 (2H, t); LCMS m/z 378 (M++1).

According to the analysis of related databases, 2475-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/52555; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 7335-27-5, name is Ethyl 4-chlorobenzoate, 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 7335-27-5, name: Ethyl 4-chlorobenzoate

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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