Month: August 2021

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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (10 g) obtained in Reference Example 2(1), 1,4-diiodobutane (19.2 g) and sodium carbonate (16.4 g) are suspended in a mixture of tetrahydrofuran (300 ml) and N,N-dimethyl acetamide (60 ml), and the mixture is stirred at 70C for 20 hours. The reaction solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane = 1/5) to give methyl trans-4-pyrrolidin-1-ylcyclohexanecarboxylate (10.9 g). APCI-MS M/Z:212[M+H]+.

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
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Application of 20921-00-0, 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 20921-00-0 as follows.

To a mixture of compound 6B (3.41 g, 14.956mmol) in THF at 0 was added CH3MgBr (32.9 mmol) . The mixture was allowed to stir at 020 for 16 hours, and then the mixture was quenched with NH4Cl, and extracted with ethyl acetate. The organic extract was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. Tthe residue obtained was purified using flash column chromatography (petroleum ether: ethyl acetate 20: 15: 1) to provide compound 6C.

According to the analysis of related databases, 20921-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YU, Wensheng; KOZLOWSKI, Joseph A.; TONG, Ling; COBURN, Craig A.; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; (101 pag.)WO2018/32467; (2018); A1;,
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Synthetic Route of 14062-24-9, 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. 14062-24-9, name is Ethyl 4-chlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 2-(alpha-ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine Add (drop by drop at 90 in a stream of nitrogen to let the alcohol escape) a solution of 4.6 g of sodium in 100 ml of ethyl alcohol to a mixture of 53.2 g of the title compound of Example 1 and 29.8 g of ethyl 4-chlorophenylacetate. Stir it for a further 4 hours at 90 and then cool it to ambient temperature. Mix the cooled reaction mixture with 100 ml of water and 100 ml of diethyl ether, collect the organic phase and dry the latter over sodium sulfate. Concentrate the dried organic phase and then distil off any excess ethyl 4-chlorophenylacetate under a high vacuum to obtain a crude yield [15.5 g (34% of theory)] of the title compound as yellow oil.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-chlorophenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US4221788; (1980); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 502764-52-5, 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. 502764-52-5 name is Diethyl dithieno[3,2-b:2′,3′-d]thiophene-2,6-dicarboxylate, 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.

152.0 g (0.446 mol) of the compound represented by the formula 3-c obtained from the above reaction formula 17 and 2.3 L of tetrahydrofuran were added to a 5 L round bottom flask, and then 95.5 g (2,277 mol) of lithium hydroxide was dissolved in 2.3 L of water, The reaction mixture was stirred for 30 minutes and then refluxed for 6 hours. After the temperature was lowered to room temperature, 3 L of 1 N hydrochloric acid was poured, and the solid was filtered, washed with methanol and dried to obtain 112.0 g (88.2%) of the compound represented by the formula 3-d.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl dithieno[3,2-b:2′,3′-d]thiophene-2,6-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SFC Ltd.; Che Jong-tae; Jeong Seong-uk; Park Seok-bae; Kang Yeong-jin; Ryu Yeon-gwon; (45 pag.)KR101791161; (2017); B1;,
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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. 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17205-02-6

3-hydroxy-cyclobutane-carboxylic acid ethyl (800 mg)In tetrahydrofuran (25mL) solution,Synthesized in Reference Example 2-53 (1) 2-chloro-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.24 g),Triphenylphosphine (5.68g),Toluene solution of diethyl azodicarboxylate (2.2M, 9.84mL) was added,It was stirred at room temperature for 13 hours. The temperature was raised to 60 , and the mixture was stirred for 7 hours at the same temperature.The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) in the purified twice, to give the title compound (2.22g) as a colorless solid .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17205-02-6.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
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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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-amino-4,5-dimethoxybenzoate

Step 1a. 6,7-Dimethoxyquinazolin-4(3H)-one (Compound 0102) A mixture of methyl 2-amino-4,5-dimethoxybenzoic acid 0101 (2.1 g, 10 mmol), ammonium formate (0.63 g, 10 mmol) and formamide (7 ml) was stirred and heated to 190~200 C. for 2 hours. Then the mixture was cooled to room temperature. The precipitate was isolated, washed with water and dried to provide the title compound 0102 as a brown solid (1.8 g, 84.7%): LCMS: m/z 207 [M+1]+; 1H-NMR (DMSO.) delta 3.87 (s, 3H), 3.89 (s, 3H), 7.12 (s, 1H), 7.43 (s, 1H), 7.97 (s, 1H), 12.08 (bs, 1H).

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2009/76022; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 581065-95-4, A common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, molecular formula is C15H31NO6, 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 compound 23-3 (33mg, 0.102 mmol), compound 12-7 (40 mg, 0.051 mmol) and 54 mu^ of diisopropylethylamine in 1 mL of DMF was added 38 mg of HATU. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was purified by HPLC to give 52 mg of compound 23-4. MS (ESI) m/z 525[M+2H], 1049[M+H].

The synthetic route of 581065-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBRX, INC.; MIAO, Zhenwei; ATKINSON, Kyle, C.; BIROC, Sandra; BUSS, Timothy; COOK, Melissa; KRAYNOV, Vadim; MARSDEN, Robin; PINKSTAFF, Jason; SKIDMORE, Lillian; SUN, Ying; SZYDLIK, Angieszka; VALENTA, Ianina; WO2012/166560; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Computed Properties of C7H13BrO2

To the mixture of the A-4 (1500 mg, 5.08 mmol) and K2C03 (1402.39 mg, 10.16 mmol) in MeCN (5 mL) was added tert-butyl 3-bromopropanoate (1062.36 mg, 5.08 mmol), and the mixture was stirred at 50 C for 16 hours. The mixture was cooled to r.t, diluted with sat.NH4Cl (50 mL), extracted with EtOAc (50 mL x 2), and the combined phase was washed over brine (20 mL), dried over Na2S04 and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 5% to 10% to 20%) to afford A-24 (1300 mg, 3.07 mmol) as an oil. 1H NMR (DMSO-d6 400MHz) deltaH = 7.83 (d, 2H), 7.72 (s, 1H), 7.47 (d, 2H), 7.43 (s, 2H), 4.10 (t, 2H), 2.75 (t, 2H), 1.31 (s, 9H).

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 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, 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. Computed Properties of C6H6N2O4

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.1. 2,4-Diphenyl-6H-furo[2,3-b]pyran-6-one (4). Reaction of 1 (85 mg, 0.5 mmol) and phenylacetylene (112 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 4 (86 mg, 60%) as a solid: mp 88-90 C; 1H NMR (300 MHz, CDCl3) delta 7.64-7.62 (4H, m), 7.55-7.52 (3H, m), 7.39 (2H, t, J=7.5 Hz), 7.30 (1H, d, J=7.5 Hz), 6.87 (1H, s), 6.21 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.6, 159.1, 154.0, 148.7, 135.3, 131.0, 129.4, 129.1, 128.5, 127.7, 123.7, 105.0, 101.0, 99.9; IR (KBr) 1724, 1607, 1526, 1379, 1295, 1195, 826, 761, 687 cm-1; HRMS m/z (M+) calcd for C19H12O3: 288.0786. Foud: 288.0790.

The synthetic route of 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6232-12-8, 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. 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 33c (600 mg, 2.24 mmol) in THF(6.0 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) andN,N-dimethylformamide (1 drop). After being stirred for 1 h atroom temperature, the mixture was concentrated in vacuo. Theresidue was resuspended in THF (6.0 mL), and to the mixture wereadded ethyl 4-(aminomethyl)benzoate hydrochloride (965 mg,4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol). After beingstirred for 12 h at room temperature, the mixture was concentratedin vacuo. The residue was taken up in ethyl acetate, washedwith 1 M hydrochloric acid (2), saturated sodium hydrogen carbonatesolution, 1 M hydrochloric acid, brine, dried over Na2SO4and concentrated in vacuo. The residue was crystallized from ethylacetate to give 34b (771 mg, 80%) as a white powder. mp 227-228 C. 1H NMR (300 MHz, DMSO-d6) d 1.31 (3H, t, J = 6.2 Hz),1.36 (3H, t, J = 6.2 Hz), 4.31 (2H, q, J = 7.1 Hz), 4.40 (2H, q,J = 7.1 Hz), 4.65 (2H, d, J = 5.5 Hz), 7.50 (2H, d, J = 8.5 Hz), 7.93(2H, d, J = 8.5 Hz), 8.57 (1H, s), 11.3 (1H, s), 13.5 (1H, s). Anal. Calcdfor C20H19N3O6S0.20H2O: C, 55.47; H, 4.52; N, 9.70. Found: C,55.50; H, 4.39; N, 9.73.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(aminomethyl)benzoate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nara, Hiroshi; Sato, Kenjiro; Naito, Takako; Mototani, Hideyuki; Oki, Hideyuki; Yamamoto, Yoshio; Kuno, Haruhiko; Santou, Takashi; Kanzaki, Naoyuki; Terauchi, Jun; Uchikawa, Osamu; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5487 – 5505;,
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