Esters-buliding-blocks

Application of 5335-05-7, A common heterocyclic compound, 5335-05-7, name is Chloromethyl benzoate, molecular formula is C8H7ClO2, 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.

(Step 2) Iodomethyl benzoate (0277) (0278) Chloromethyl benzoate (10.0 g, 58.8 mmol) was dissolved in acetonitrile (70.0 ml), sodium iodide (17.6 g, 117 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 24 hours. Acetonitrile was distilled off under reduced pressure, and diethyl ether was added. The precipitated solid was filtered off, washed with diethyl ether, and dried under reduced pressure, and then purified by silica gel column chromatography (petroleum ether:ethyl acetate=30:1 to 10:1) to obtain the title compound (14.5 g, 94%). (0279) 1H NMR (CDCl3, 400 MHz): delta 8.06-8.04 (m, 2H), 7.64-7.62 (m, 1H), 7.49-7.44 (m, 2H), 6.17 (s, 2H)

The synthetic route of 5335-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ajinomoto Co., Inc.; UENO, Hirokazu; YAMAMOTO, Takashi; MIYAZAWA, Tomoko; SHINKAI, Kenji; ARISAKA, Harumi; TAKANOHASHI, Toshiyuki; (122 pag.)US2016/244451; (2016); A1;,
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Electric Literature of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

Step A: ethyl 4-(5 -bromopyridin-2-yloxy)cycl ohexanecarboxylateTo a solution of 5-bromo-2-hydroxypyridine (1.0 g, 5.747 mmol) and ethyl 4- hydroxycyclohexanecarboxylate (0.99 g, 5.75 mmol) in THF (50 mL) was added PPh3 (2.4 g,9.15 mmol) and DIAD (1.8 mL, 9.14 mmol). The reaction mixture was stirred at RT for 17 h.The solution was then concentrated and purified by silica gel column chromatography with anISCO system to yield ethyl 4-(5-bromopyridin-2-yloxy)cyclohexanecarboxylate as a colorless oil.

Statistics shows that trans-Ethyl 4-hydroxycyclohexanecarboxylate is playing an increasingly important role. we look forward to future research findings about 3618-04-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; ASLANIAN, Robert; CAO, Jianhua; KIM, David; ZORN, Nicolas; WO2012/24179; (2012); A1;,
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These common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, 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. Formula: C7H15NO2

Bromoacetyl bromide (3.56 g, 17.6 mmol,1.55 ml, 1.5 equivalent), dry CH2C12 (50 ml) and K3P04 (6.41 g, 30.2 mmol, 2.5 equ.) was mixed in a flask of 250 ml under N2 atmosphere. Sarcosine tert-butyl ester (1.7 g, 11.7 mmol, 1.0 equivalent) was dissolved in dry CH2C12 (20 ml) and was added dropwise to dichloromethane solution of bromoacetyl bromide at 0 C in 30 minutes, then the reaction mixture was stirred for additional 12 hours at room temperature under N2 atmosphere before the aqueous HC1 solution (0.5 M, 30 ml) was added to the reaction mixture. After the addition of RC1 solution, the reaction mixture was stirred for additional 5 minutes, then the two phases were separated using a separatory funnel. The aqueous phase was washed with CH2C12 (1 x 15 ml) and then the unified organic phases were washed with KHCO3 solution (2 x 30 ml, 10 mlm%) and saturated NaC1 solution(1 x 30 ml). The organic phase was dried with MgSO4, then dichioromethane was evaporated at reduced pressure, and the crude product was stored at -20 C until further use. Yield: 2.01 g (65%). ?H NMR [360 MHz, CDCl3] oe 1.6 (9H, s, CR3) 2.8 (3H, s, CR3), 4.01 (2H, s, CH2), 4.4 (2H, s, CR2)

The synthetic route of tert-Butyl 2-(methylamino)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DEBRECENI EGYETEM; BOTAR, Richard; GARDA, Zoltan; FODOR, Tamas; KALMAN, Ferenc Krisztian; NAGY, Viktoria; TIRCSO, Gyula; TOTH, Imre; (44 pag.)WO2017/89847; (2017); 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. 4630-82-4, name is Methyl cyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Formula: C8H14O2

Several others esters (see Table 3) were hydrogenated under identical conditions as reported in Table 4 with RuCl2(L-I)2. The reaction conditions were identical to those reported above for methyl benzoate.Table 3: Structure and name of substrates used EPO Table 4: Results obtained using the general conditions described above EPO Conversion: (in %, analysed by GC after silylation) of ester to alcohol after 2h 30min. Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I)2 0.05 mol%, NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

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; FIRMENICH SA; WO2006/106483; (2006); A1;,
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These common heterocyclic compound, 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, 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. category: esters-buliding-blocks

Example 31: N-f5-Chloro-2 (at)(E -3-f3-(at)4-fluoro-benzvl)-3,8-diaza-bicvclof3.2.11oct-8-yll-3-oxo- proaen I(at)(1-h droxy-1-methvl-ethyl -ahenyl-acetamide; a) 4-Amino-5-bromo-2-chloro-benzoic acid methyl ester; 4-Amino-2-chloro-benzoic acid methyl ester (7.8 g, 42.0 mmol) is dissolved in 300 ml THF. At room temperature 8.97 g (50.4 mmol) N-bromsuccinimide are added in portions. After stirring over night at room temperature, 200 ml ethyl acetate are added and the organic layer is washed first with 10% sodium thiosulfate solution followed by 10% sodium carbonate solution and saturated sodium chloride solution. The title compound is purified by chromatography (Si02, ethyl acetate/c-hexane 1/9) and is isolated as a yellow solid (3.70 g, 33%) 1 H-NMR (400MHz; DMSO-d6) : 3.75 (s, 3H) ; 3.15-3.25 (m, 1 H); 6.35 (s, 1 NH); 6.83 (s, 1 H); 7.88 (s, 1 H). MS (m/z) ES-: 264 ([M-H] -, 100).

The synthetic route of Methyl 4-amino-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/103054; (2005); A2;,
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Synthetic Route of 42122-75-8, 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. 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example (Ik-2) 2-Chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoic acid 6.74 g (36.3 mmol) of methyl 5-amino-2-chlorobenzoate, 0.22 g (1.8 mmol) of 4-N,N-dimethylaminopyridine and 9.49 ml (54.4 mmol) of N-ethyldiisopropylamine are dissolved in 50.0 ml of ethyl acetate and cooled to 0 C. A solution of 6.0 g (18.1 mmol) of 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride in 100 ml of ethyl acetate is added over the course of an hour to this reaction mixture. When the addition is complete, the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with 250 ml of ethyl acetate and the organic phase is then washed three times with in each case 100 ml of 1M hydrochloric acid, three times with 1M sodium hydroxide solution and once with saturated sodium chloride solution. This gives 8.0 g of a mixture of methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate and methyl 5-(bis{[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)-2-chlorobenzoate in the ratio 6:4.

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, Methyl 5-amino-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience AG; US2011/301181; (2011); A1;,
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Application of 1000342-11-9,Some common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, molecular formula is C9H10BrNO2, 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.

01035] Step 4: methyl 3-bromo-5-(cyclopentylamino)benzoate[01036] To a stirred solution of ethyl 3-amino-5-bromobenzoate (2 g, 8.73 mmol) and cyclopentanone (2.2 g, 26.1 mmol) in methanol (20 mL), acetic acid (1.04 g, 17.4 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.37 21.83 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford desired compound ( 1 .6 g, 61 %).

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-amino-5-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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Electric Literature of 18013-97-3, A common heterocyclic compound, 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, molecular formula is C12H12Br2O4, 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.

60 g (160 mmol) of diethyl dibromoterephthalate, 43 g (320 mmol) of o-tolylboronic acid, 365 mg (0.32 mmol) of Pd(PPh3)4 and 92 g (660 mmol) of K2CO3 are heated at the boil for 4 h in 300 ml of toluene and 300 ml of water. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4. The residue remaining is recrystallised twice from heptane to give colourless crystals. The yield is 51 g (127 mmol, 81%).

The synthetic route of 18013-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; US2011/92701; (2011); A1;,
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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. 10602-06-9, name is Methyl 3-ethynylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 3-ethynylbenzoate

General procedure: To a solution of 9 (9.1 mmol) in THF (18 mL) at room temperature were added alkyne S4-6 (2.0 mL, 14 mmol), PdCl2(PPh3)2 (320 mg, 0.46 mmol), CuI (174 mg, 0.92 mmol) and Et3N (2.5 mL, 18 mmol). After being stirred at room temperature for 1 h, the reaction mixture was quenched with saturated aqueous NH4Cl. The mixture was extracted with AcOEt, washed with saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4, and concentrated. The residue was purified with flash column chromatography to give 10. To a solution of 10 (50 mmol) in MeOH/AcOH (9/1, 1.0 mL) was added Pd(OH)2/C (20%, 35 mg). After being stirred under H2 at room temperature for 5 h, the mixture was filtered through a pad of Celite. The residue was washed with MeOH, and the filtrate was concentrated. The resulting solid was dissolved in 10 mM aqueous monoethanolamine, and purified with high performance liquid chromatography (column: Asahi-pak ODP-50 10E 10 x 250 mm; flow rate 2.0 mL/min; 0-20% MeCN/10 mM monoethanolamine-AcOH pH 9 buffer; detection: UV 254 nm) to give 4a, 4v, 4w, 4dd, 5q-s, 5z, 5aa, 5cc or 6a as monoethanolamine salt.

The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Inaoka, Daniel Ken; Iida, Maiko; Honma, Teruki; Harada, Shigeharu; Nara, Takeshi; Balogun, Emmanuel Oluwadare; Kita, Kiyoshi; Hashimoto, Satoshi; Tanaka, Akiko; Kita, Kiyoshi; Tabuchi, Toshiyuki; Kuranaga, Takefumi; Inoue, Masayuki; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1465 – 1470;,
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Reference of 33689-29-1, These common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, 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 stirred 0 C solution of methyl l -hydroxyeyclopropane-I- carboxylate (1 16 mg, 1.00 mmol, 1.00 equiv) in DMF (4 mL) was added sodium hydride (60 mg, 1.50 mmol, 1.50 equiv, 60% in mineral oil) in several batches. The resulting reaction mixture was stirred for 0.5 h at 0 C, then 2-(bromomethyl)-l,4- dichlorobenzene (238 mg, 0.99 mmol, 0.99 equiv) was added. The resulting reaction mixture was stirred for 1 h at room temperature and quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with, brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide 270 mg (98%) of 85a as a yellow oil.

The synthetic route of 33689-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
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