Esters-buliding-blocks

Synthetic Route of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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 stirred solution of carboxylic acid 10 (30 mg, 0.125 mmol), HATU (53 mg, 1.38 mmol) and DIPEA (70 L, 0.375 mmol) in DMF (5 mL) at 25 C was added the corresponding primary amine (33 mg, 0.138 mmol). The reaction mixture was stirred for 16 h, diluted with 0.1 N aqueous NaOH (15 mL) and extracted with CH2C12 (3 x 20 mL). The combined organic phases were dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-5 % MeOH in DCM) to give compound M (18 mg, 0.040 mmol, 32% yield). MS (ESI) m/z 456 (M+H)+

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; GRAY, Nathanael S.; HAGGARTY, Stephen J.; CAI, Quan; TELO BAPTISTA LIMA DA SILVA, Maria Catarina; ZHANG, Tinghu; FERGUSON, Fleur M.; (220 pag.)WO2019/14429; (2019); A1;,
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Related Products of 89-71-4, A common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

Placed in a 20L reaction vessel was petroleum ether, o-methyl benzoate, N- bromosuccinimide. Use a water bath to control temperature at 15 deg.C. Under stirring, react for 2.5h. Using known separation methods, separated o halomethyl benzoate.

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; Suzhou Huanghe Pharmaceutical Co., Ltd.; Su, Zixuan; Qu, Xiaoming; Xiao, Zuhua; (16 pag.)CN105330639; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, 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 1150566-27-0, category: esters-buliding-blocks

To a suspension of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (I-7) (128 mg, 0.565 mmol) in DMSO (2.5 mL) was added (3S)-3-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine (I-53) (167 mg, 0.565 mmol) and potassium floride (328 mg, 5.65 mmol). The mixture was heated at 120 C. overnight. The mixture was poured into water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield ethyl 6-((3S)-2-(3-fluorophenyl)-3-hydroxypyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxylate (I-54). MS m/z 371.1 (M+1)+.

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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; US2012/65184; (2012); A1;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14273-90-6, name is Methyl 6-bromohexanoate, 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 14273-90-6, Quality Control of Methyl 6-bromohexanoate

(1) 1,2,3,4-Tetrahydroquinoline (0.50 mL, 3.98 mmol) and methyl 6-bromohexanoate (0.76 mL, 4.78 mmol) were added to MeCN (30 mL) containing KI (1.59 g, 9.58 mmol) and K2CO3 (1.10 g, 7.96 mmol) dissolved therein, and the suspension was stirred at 100 C. for 21 hours in an argon atmosphere. The reaction solution was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic phase was washed with saturated saline, dried over Na2SO4, and dried under reduced pressure. The residue was purified by flash column chromatography (hexane/EtOAc=100/0 to 80/20) to obtain N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline (1.10 g, 100%). Colorless oil; 1H NMR (500 MHz, CDCL3) delta: 7.02 (t, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 6.51-6.54 (m, 2H), 3.66 (s, 3H), 3.20-3.26 (m, 4H), 2.73 (t, J=6.3 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.90-1.94 (m, 2H), 1.63-1.69 (m, 2H), 1.56-1.62 (m, 2H), 1.32-1.38 (m, 2H); LRMS (ESI): m/z calcd [M+H]+ 262.2, found 262.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JAPAN SCIENCE AND TECHNOLOGY AGENCY; KANAI, Motomu; SOMA, Yohei; TANIGUCHI, Atsuhiko; SHIMIZU, Yusuke; (45 pag.)US2017/197956; (2017); A1;,
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927-68-4, name is 2-Bromoethyl acetate, 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. Quality Control of 2-Bromoethyl acetate

To a solution of the product of step 1(143 mg, 0.69 mmol) in DMF (1.5 mL) at 0 C, wasadded NaH (60% suspension in mineral oil, 30 mg, 0.76 mmol). The mixture was stirred for 0.5 h followed and 2-bromoethyl acetate (184 mg, 0.12 mL, 1.1 mmol) was added. The reaction was brought to room temperature and stirred overnight. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2504, and concentrated underreduced pressure. The residue was purified by silica gel column chromatography (0-20% gradient MeOH in CH2C12) to afford the title compound (180 mg, 89%) as a colorless oil.?H NMR (500 MHz, CDC13) oe 1.36 (t, J=7.4 Hz, 3H), 1.89-2.00 (m, 2H), 2.03-2.15 (m, 5H), 2.75-2.82 (m, 2H), 2.89 (t, J=6.3 Hz, 2H), 3.99 (q, J=7.4 Hz, 2H), 5.25 (s, 2H)

The synthetic route of 927-68-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, I.; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (374 pag.)WO2016/109706; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 18595-12-5, HPLC of Formula: C9H11NO2

Methyl 5-amino-2-methylbenzoate (1.0 eq, 3.75 g) was dissolved in acetic acid (70 ml). N-Iodosuccinimide (1.0 eq, 5.27 g) was added portionwise over 60 minutes. The mixture was stirred at room temperature for 30 minutes. Acetic acid was evaporated. The residue was diluted with ethyl acetate (80 ml) and neutralized with saturated sodium carbonate (80 ml). The organic layer was washed with 1M sodium thiosulfate (2¡Á40 ml), then water (2¡Á40 ml) and brine (2¡Á40 ml). The material was purified by flash chromatography on silica gel (gradient 10% to 30% ethyl acetate in hexanes) to provide methyl 5-amino-4-iodo-2-methylbenzoate as a yellow-orange solid (3.19 g, 49% yield). GCMS>95% pure, m/z 291. 1H NMR (400 MHz, DMSO, d6) delta 2.30 (s, 3H), 3.78 (s, 3H), 5.27 (br s, 2H), 7.24 (s, 1H), 7.54 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P.; US2009/239859; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 15441-07-3,Some common heterocyclic compound, 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, molecular formula is C4H7ClO4S, 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.

EXAMPLE 14 N-isobutyl-3-amidosulfopropionic Acid To 14.6 parts of isobutylamine and 100 parts of water there are added dropwise at 0 C, with stirring 18.65 parts of methyl 3-chlorosulfonylpropionate and then simultaneously from separate dropping funnels 18.65 parts of methyl 3-chlorosulfonylpropionate and 54 parts of 14.8% caustic soda solution. Stirring is continued for a further hour at 0 C and 4 hours at room temperature; 8.8 parts of sodium hydroxide are added and the mixture is heated at 60 C for 4 hours. The reaction mixture is acidified with a 2N H2 SO4 solution to a pH of 1 and the resulting precipitate is filtered off, washed with 100 parts of water and dried at 40 C/25 mm. Yield: 24.6 parts (59% of theory) of white crystalline N-isobutyl-3-amidosulfopropionic acid, m.p. 132-134 C (after recrystallization from H2 O).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-(chlorosulfonyl)propanoate, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4060522; (1977); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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. Product Details of 110661-91-1

General procedure: To 100 mLrbf was added a mixture of compound 20 (1.66 g, 10 mmol), cesiumcarbonate (3.26 g, 10 mmol), TBAI (3.70 g, 10 mmol) and anhydrousDMF (20 mL). Compound 19 (2.23 g, 10 mmol) was added dropwise tothe mixture. The reaction mixture was then stirred at room temperaturefor 3 h. Ethyl acetate was added into the reaction mixture. The combinedmixture was washed with two portions of water. After evaporationof the solvent under reduced pressure MeOH (20 mL) was addedfollowed by silica gel (1 g). The resulting plug was loaded on to a silicagel column and eluted with 1:10 (ethyl acetate: hexane). Fractions withand Rf = 0.64 (hexane:ethyl acetate 1:1) were pooled and evaporatedto afford tert-butyl esters (1.47 g, yield; 47%). Trifluoroacetic acid wasthen added into the tert-butyl esters and mixture was stirred at roomtemperature for 30 min. Excess of trifluoroacetic acid was evaporatedand MeOH (20 mL) was added followed by silica gel (1 g). The resultingplug was loaded on to a silica gel column and eluted with 1:10 (ethylacetate: hexane). Fractions with and Rf = 0.45 (TLC) (Hexane: ethylacetate,1:1) were pooled and evaporated to afford 22 (1 g, yield 83%)as white solid.

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

Reference:
Article; Dekhne, Aamod S.; Gangjee, Aleem; Golani, Lalit K.; Hou, Zhanjun; Islam, Farhana; Matherly, Larry H.; O’Connor, Carrie; Bioorganic and medicinal chemistry; vol. 28; 12; (2020);,
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Reference of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

Statistics shows that Methyl 2,2-dimethoxyacetate is playing an increasingly important role. we look forward to future research findings about 89-91-8.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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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. 50893-36-2, name is 1-Chloroethyl ethyl carbonate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H9ClO3

Reference Example 19 To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-tetrazol-1-yl)phenyl]-2-imidazolidinone (0.61 g) and 1-chloroethyl ethyl carbonate (3.7 g) was added acetonitrile (1 ml), and the mixture was stirred for 38 hours at 95¡ã C. The reaction mixture was concentrated under reduced pressure. To the residue was added diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The elude was concentrated in vacuo. The residue was dissolved in water (10 ml), and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[-1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride (Compound 7,90 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 1.21,1.22(3H,t,J=7 Hz), 1.79,1.80(3H, d,J=6 Hz), 3.62-4.23(6H,m), 4.65-5.10(3H,m), 6.69-6.82(2H,m), 6.94-7.04(1H,m), 7.26-7.38(2H,m), 7.90(4H,s), 9.23(0.5H,s), 9.27(0.5H,s), 10.08(1H,s), 10.72(0.5H,s), 10.82(0.5H,s).

According to the analysis of related databases, 50893-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6583164; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics