Month: August 2021

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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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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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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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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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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Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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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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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrFO2

Step b) Methyl 4-acetoxy-3-fluorobenzoate (9b) Allyl chloride (105 muL, 1.28 mmol) and TFA (20 muL, 0.26 mmol) were added to a suspension of zinc dust (480 mg, 7.34 mmol) and anhydrous cobalt(II) bromide (96.6 mg, 0.44 mmol) in MeCN (4 mL), under inert gas. After stirring at room temperature for 10 min, the aryl bromide (1.003 g, 4.30 mmol dissolved in 5 mL MeCN) from (a) was added, followed by acetic anhydride (0.45 mL, 4.79 mmol) and more MeCN (1 mL). The mixture was stirred overnight, quenched with 1M HCl (20 mL), and then extracted with EtOAc (3*20 mL). The organic phase was washed successively with saturated aqueous NaHCO3 (20 mL) and saturated NaCl (2*20 mL), dried (Na2SO4), and concentrated. Flash chromatography (silica, 6/1 to 4/1 petroleum ether-EtOAc gave recovered bromide (161.1 mg, 16%) and the desired ketone (white solids, 305.5 mg, 36%). NMR (CDCl3) delta ppm: 1H (400 MHz) 7.94-7.86 (m, 2H), 7.80 (dd, 1H, J=11.2, 1.6 Hz), 3.95 (s, 3H), 2.67 (d, 3H, J=4.4 Hz); 19F (376 MHz)-109.2 (m); 13C (100 MHz) 195.4 (d, J=3.7 Hz), 165.1 (d, J=2.2 Hz), 161.6 (d, J=255 Hz), 135.8 (d, J=8.1 Hz), 130.7 (d, J=2.9 Hz), 129.0 (d, J=14 Hz), 125.2 (d, J=3.6 Hz), 117.9 (d, J=26 Hz), 52.7 (s), 31.4 (d, J=7.3 Hz).

According to the analysis of related databases, 849758-12-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nilsson, Magnus; Oden, Lourdes; Kahnberg, Pia; Grabowska, Urszula; US2009/23748; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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.

According to a general procedure for formation of a Weinreb intermediate,36 a vigorously stirred slurry of methyl dimethoxyacetate (4, 200 ^iL, 1.64 mmol) and N, O-dimethylhydroxylamine hydrochloride (201 mg, 2.05 mmol) in THF (2.4 mL) under argon was treated dropwise with isopropylmagnesium bromide (2.05 mL, 4.10 mmol, 2 M solution in THF) at -20 C. The resulting heterogeneous reaction mixture was stirred for 1.5 h at -20 C under argon. The reaction mixture was quenched with saturated aqueous NH4C1 and H20 (1 : 1). After extraction with ether (3 x 50 mL), the combined organic extract was washed (brine), dried (Na2S04) and concentrated under vacuum at room temperature. The ? NMR spectrum of the crude product showed unreacted 4 and signals consistent with those reported for l,l-dimethoxy-3-methylbutan-2-one (A).

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

Reference:
Patent; NORTH CAROLINA STATE UNIVERSITY; LINDSEY, Jonathan S.; MASS, Olga; WO2013/62670; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics