Category: esters-buliding-blocks

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. 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Formula: C9H8F3NO2

To a mixture of methyl 3-amino-4-(trifluoromethyl)benzoate (15 g, 0.073 mol) and aqueous HC1 solution (i2 M, 24 mL) in H20 (i00 mL) at 0 C was added dropwise a solution of NaNO2 (5.5 g, 0.080 mol) in H20 (30 mL). The reaction was stined at 0 C for 30 mm and then added dropwise to a sluny of CuCN (7.1 g, 0.080 mol) and KCN (8.4 g, 0.i3 mol) in H20 (200 mL), while maintaining the internal temperature between 5-1 0 C. After the addition was complete, the reaction was heated at 80 C for 1 h. The mixture was cooled and the solution was extracted with EtOAc (200 mL x 4). The combined organic layers were dried over anhydrous Na2504 and concentrated. The residue was purified by column chromatography on silica gel (2% EtOAc in PE) to afford the title compound. MS: m/z = 230.0 (M + 1). ?H NMR (400 MHz, CDC13)oe 8.46-8.53 (m, 1H), 8.33-8.42 (m, 1H), 7.87-7.95 (m, 1H), 4.01 (s, 3H).

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; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
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Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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. Recommanded Product: 935273-86-2

Benzyl 3,3-difluorocyclobutanecarboxylate (2-C) (0.84 g, 3.72 mmol) was dissolved in ethanol (40 ml), and approximately 20 mg of palladium on activated carbon was added. The mixture was stirred at room temperature under hydrogen atmosphere for 12 hours, and then filtered through a pad of Celite. The filtrates were concentrated and dried in vacuo to give 2-D. lH NMR (500 MHz, CDCI3): delta2.86-2.93 (4H, m), 3.02-3.04 (IH, m) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935273-86-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/47625; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 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 581065-95-4, name: tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

To a solution of Compound 6a (66 mg, 0.2 m mole) in dichloromethane (1 mL) were added DCC (47 mg, 0.22 m mole), HOBt (31 mg, 0.22 mmole) and the compound 4 (50 mg, 0.2 m mole). The mixture thus obtained was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by flash chromatography on silica gel with 1 % methanol in dichloromethane as eluent to give the title compound as an yellow oil (70 mg, 62%). ¹H NMR 8 1.44 (s, 9H), 2.51 (t, 1H), 2.63 (t, 2H), 2.93 (d, 3H), 3.01 (t, 2H), 3.45 (m, 2H), 3.55 (m, 2H), 3.64 (m, 12H), 3.71 (t, 2H), 5.01 (bs, 1H), 6.38 (bt, 1H), 6.62 (m, 2H), 7.27 (m, 1H), 7.43 (dd, 1H). MS (ES) 491 (M-56+H+), 513 (M- 56+Na+), 547 (M+H+), 569 (M+Na+) Compound 11b: ¹H NMR 8 1.34 (d, 3H), 1.45 (s, 9H), 2.30 (m, 1H), 2.5 (t, 2H), 2.69 (m, 1H), 2.93 (d, 3H), 3.37-3.55 (m, 5H), 3.63 (m, 12H), 3.71 (t, 2H), 4.99 (bs, 1H), 6.13 (bt, 1H), 6.62 (m, 2H), 7.25 (m, 1H), 7.48 (dd, 1H). MS (ES) 505 (M-56+H+), 527 (M-56+Na+), 543 (M-56+K+), 561 (M+H(at), 583 (M+Na(at). Compound lie: 1.43 (s, 3H), 1.45 (s, 9H), 2.46 (s, 2H), 2.5 (t, 2H), 2.92 and 2.94 (2s, 3H), 3.33 (m, 2H), 3.47 (t, 2H), 3.63 (m, 12H), 3.70 (t, 2H), 6.06 (bt, 1H), 6.63 (m, 2H), 7.25 (m, 1H), 7.54 (d, 1H); MS (ES) 519 (M-56+H(at), 541 (M-56+Na+), 575 (M+H(at), 597 (M+Na+).

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 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDAREX, INC.; WO2005/112919; (2005); A2;,
Ester – Wikipedia,
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Application of 56441-97-5, A common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, 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.

Commercially available methyl 4-hydroxy-3-methoxy-benzoate 1 was converted in 5 steps to 4-(3-fluoroanilino)-6-methoxy-7-benzyloxy-quinazolme 15 (35% overall yield).[17,18] The only significant modification involved an improved workup of the nickel chloride hexahydrate-sodium borohydride reduction of the nitro intermediate. Debenzylation with trifluoroacetic acid to give the 7-hydroxy intermediate 16, followed by alkylation with propargyl bromide in acetonitrile, gave 13 in a 65% yield for 2 steps. This method involved an additional step, and the overall yield was greater. In addition, the final 7-hydroxy intermediate 16 could be used to generate other products [19].

The synthetic route of 56441-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; HANSON, Robert, N.; WO2010/85747; (2010); A1;,
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Electric Literature of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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: To a solution of compounds 1a-1e or methyl 4-aminobenzoate (1.0 mmol) in pyridine (3.0 mL), the corresponding sulfonyl chloride (1.3 mmol) in pyridine (3.0 mL)were added dropwise under nitrogen atmosphere at 0 C, then the reaction mixture was stirred at room temperature overnight. The reaction was then acidified to pH=1 with 4NHCl(aq) and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography (ethyl acetate-petroleum ether = 1:2) to give the title compounds 2a-2i.

Statistics shows that Methyl 4-chlorosulfonylbenzoate is playing an increasingly important role. we look forward to future research findings about 69812-51-7.

Reference:
Article; Zhang, Jiankang; Shen, Luqing; Wang, Jincheng; Luo, Peihua; Hu, Yongzhou; Medicinal Chemistry; vol. 10; 1; (2014); p. 38 – 45;,
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Some common heterocyclic compound, 14062-19-2, name is Ethyl p-Tolylacetate, molecular formula is C11H14O2, 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. COA of Formula: C11H14O2

LiHMDS was prepared by the treatment of HMDS (2.432 g, 15.07 mmol) with n-BuLi (1.6 M solution in hexane, 9.4 mL, 15 mmol) in dry THF (30 mL) at 0C for 30 min. To a solution of ethyl p-tolylacetate (1.778 g, 9.98 mmol) in dry THF (30 ml) was added the LiHMDS at -78C. The mixture was stirred at -78C for 30 min. To the mixture, ethyl cyanoformate (1.110 g, 11.20 mmol) was added at -78C, and then the mixture was allowed to warm to 0C for 80 min. 10% HCl was added at 0C, and the mixture was extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4. After removal of the solvent, the residue was purified by column chromatography using silica gel (hexane/acetone 25/1) to afford 7 as a colorless oil (2.396 g, 96%). 1H NMR spectra data were identical to those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-19-2, its application will become more common.

Reference:
Article; Kawasaki, Masashi; Kuroyanagi, Saki; Ito, Takuya; Morita, Hiroyuki; Tanaka, Yasuo; Toyooka, Naoki; Tetrahedron; vol. 73; 15; (2017); p. 2089 – 2099;,
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Related Products of 14273-90-6,Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, 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 4-piperidone (0.125 g, 1.26 mmol) in anhydrous DMF (2 ml), K2CO3 (0.2 g, 1.51 mmol), 21 (0.52 g, 2.48 mmol) and KI (0.015 g, 0.090 mmol) were added to the mixture. The reaction mixture was stirred at r.t. for 36 hours under N2. The reaction mixture was filtered off and filtrate was concentrated and dried under vacuum providing a white solid (0.29 g, 98%) of compound 22. Product was used without further purification to the next step. (0431) 1H NMR (400 MHz, Chloroform-d) delta: 3.64 (d, J=2.0 Hz, 3H), 3.38 (t, J=6.7 Hz, 2H), 2.70 (t, J=6.2 Hz, 2H), 2.42 (t, J=6.8 Hz, 4H), 2.30 (t, J=7.4 Hz, 4H), 1.85 (p, J=7.0 Hz, 2H), 1.70-1.56 (m, 4H).

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

Reference:
Patent; Ecole Polytechnique Federale de Lausanne (EPFL); Sinisi, Riccardo; Morales Morales, Alma Rosa; Dubikovskaya, Elena A.; Singh, Rajendra; (103 pag.)US2018/79906; (2018); A1;,
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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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Synthesis Example 40 Synthesis of N-propargyltrifluoroacetamide Propargylamine (Aldrich, 25 g, 0.45 mol) was added dropwise to methyl trifluoroacetate (Tokyo Chemical Industry Co., Ltd., 69.2 g, 0.54 mol) cooled to 0 C. They were allowed to react at 0 C. for two hours to afford 43.8 g (86.0%) of N-propargyltrifluoroacetamide after purification by vacuum distillation (23 mmHg, boiling point; 77 C.).

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; The Institute of Physical and Chemical Research; US6365350; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 23680-40-2, A common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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.

A solution of 2-methylfuran (15.7mL, 174 mmol) andmethyl 3-bromopropiolate 11 (7.10 g, 43.6 mmol) incyclohexane (100 mL) was refluxed for 1 d. Afterremoval of the solvent, the resulting mixture of 12aand 12b was used in the next step without purification.12a: 1H NMR (300 MHz, CDCl3) delta 1.89 (3H, s),3.79 (3H, s), 5.21 (1H, d, J = 1.8 Hz), 6.99 (1H, d,J = 5.1 Hz), 7.14 (1H, dd, J = 1.8, 5.1 Hz); 13C NMR(75 MHz, CDCl3) delta 16.43, 51.65, 87.98, 91.49, 142.12,146.96, 149.94, 153.89, 163.49.The ratio of 12a:12b was determined to be 11:1based on 1H NMR analysis. The signal due to 1-Me of12b was observed at delta = 1.74.

The synthetic route of 23680-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Konishi, Shunsuke; Mori, Naoki; Takikawa, Hirosato; Watanabe, Hidenori; Bioscience, Biotechnology and Biochemistry; vol. 83; 3; (2019); p. 391 – 399;,
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Related Products of 87661-20-9, 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. 87661-20-9 name is tert-Butyl cyclopropanecarboxylate, 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.

c) 1 -r(2S,5R)-5-r4-(3-Methoxy-propyl)-2,2-dimethyl-3,4-dihvdro-2H- benzori ,41oxazin-6-ylmethoxy1-1 -(toluene-4-sulfonyl)-piperidin-2-ylmethyl1- cvclopropanecarboxylic acid tert-butyl ester; A solution of 5.00 mmol of cyclopropanecarboxylic acid tert-butyl ester [87661 -20-9] in 50 ml of tetrahydrofuran at -78C is treated with 5.5 mmol of lithium diisopropyl- amine. The reaction mixture is stirred at -78C for 4 hours before the addition of a solution of 6.00 mmol of 6-[(3R,6S)-6-bromomethyl-1 -(toluene-4-sulfonyl)-piperidin-3- yloxymethyl]-4-(3-methoxy-propyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1 ,4]oxazine in 10 ml of tetrahydrofuran. The reaction is stirred at -78C for 1 hour, then allowed to warm to room temperature over 4 hours, and quenched with saturated aqueous ammonium chloride solution. The mixture is extracted with tert butyl-methyl ether (3x), the combined organic extracts are dried with sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl cyclopropanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2009/106599; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics