Category: esters-buliding-blocks

Electric Literature of 40876-98-0,Some common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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 of0.01 mol of diethyl oxalylacetate sodium salt, 0.01 molof aromatic aldehyde, and 0.01 mol of urea was heatedat reflux in 10 mL of acetic acid for 2 h. The mixturewas kept for 24 h at room temperature, the precipitatewas filtered off and recrystallized from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, its application will become more common.

Reference:
Article; Gein; Zamaraeva; Volkova; Dmitriev; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 730 – 733; Zh. Org. Khim.; vol. 52; 5; (2016); p. 740 – 743,4;,
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Related Products of 107045-28-3, A common heterocyclic compound, 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, molecular formula is C12H17NO2, 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 solution of 2-(2,6-dioxopiperidin-3 -yl)-4-fluoroi soindoline- 1,3 -dione (2-1,200 mg, 0.724 mmol, 1 equiv) inNMP (3.6 mL, 0.2 M)was added DIPEA (525 jiL, 1.45 mmol,2 equiv) and tert-butyl 4-(aminomethyl)benzoate (165 mg, 0.796 mmol, 1.1 equiv). The reactionmixture was heated to 90 C overnight and then cooled to room temperature. EtOAc (50 mL)was added and the organic layer was washed with water (30 mL) and brine (3 x 30 mL), driedover Na2504, filtered, and concentrated in vacuo. The residue was purified by flash column

The synthetic route of 107045-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; BUCKLEY, Dennis; ISHOEY, Mette; WINTER, Georg; (195 pag.)WO2018/98280; (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. 35180-01-9, name is Chloromethyl isopropyl carbonate, A new synthetic method of this compound is introduced below., name: Chloromethyl isopropyl carbonate

A method for synthesizing tenofovir disoproxil, in a dry and clean 1000 mL three-neck reaction flask with mechanical stirring, after nitrogen substitution, 500 mL of N, N-dimethylacetamide was added at room temperature, and tenofovir (PMPA ) 86.1g (0.3 mol, 1.0 equiv), triethylamine 60.6g (0.6 mol, 2.0 equiv), tetrabutylammonium bromide 9.7g (0.03 mol, 0.1 equiv), urea 18.2g (0.3 mol, 1.0 equiv) After stirring for 30min, the temperature was raised to 50 ~ 60 C, and 137.2g (0.9mol, 3 equiv) of POC was slowly added dropwise. After the dropwise addition was completed, the reaction was continued for about 3 hours. After the temperature was lowered, the reaction solution was flushed into 2000mL of ice brine, and stirred Hours, filtered to obtain crude tenofovir dipyrfurate, then beaten once with 300 ml of isopropyl acetate, filtered, and dried to obtain 127.8 g of tenofovir dipyrfurate, purity 98.5%, yield 82.0%.

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aoruite Pharmaceutical Co., Ltd.; Xu Tingjun; Xie Xiaoqiang; Liu Xijing; Zhou Tianxi; Xu Xiaobo; (7 pag.)CN110590842; (2019); A;,
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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. 2876-78-0, name is Methyl 1-Naphthaleneacetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 1-Naphthaleneacetate

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetates 3 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.) and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture was added DBU (456 mg, 3 mmol, 3.0 equiv.). The mixture was stirred for 12 hours at room temperature till the reaction was complete. To the resulting mixture was added saturated ammonium chloride solution (25 mL), and the mixture was then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 4 was purified using column chromatography on silica gel using an appropriate eluent.

According to the analysis of related databases, 2876-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step c) 4-[(Biphenyl-2-carbonyl)-amino]-2-methoxybenzoic acid methyl ester Into a refluxing solution of 2-biphenylcarboxylic acid (9.2 g, 46 mmol) in dichloromethane was added dimethylformamide (0.1 ml, 1.4 mmol) and then neat oxalyl chloride (8.1 ml, 92 mmol) via syringe. The reaction was refluxed for 10 min, then the volatiles removed in vacuo. The residue was redissolved in dichloromethane, concentrated and dried under high vacuum for 15 min. The acid chloride was dissolved in dichloromethane (50 ml) and added into a 0° C. solution of 4-amino-2-methoxy-benzoic acid methyl ester (8.4 g, 46 mmol), diisopropyl ethylamine (10.5 ml, 60 mmol) and dichloromethane (200 ml). The reaction was warmed to room temperature and stirred for 16 hours. The reaction was diluted with dichloromethane, washed with water, (1N) sodium hydroxide (1N) HCl and brine, and dried (MgSO4). Evaporation gave a yellow foam, which was crystallized from methanol to give a light yellow solid (16.08 g, 96percent) m.p. 141°-142° C. Analysis for: C22 H19 N O4 Calcd: C, 73.12; H, 5.30; N, 3.88. Found: C, 72.93; H, 5.20; N, 3.83.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US5753648; (1998); 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

[3-F [ (4-CHLOROPHENYL)] (methyl) amino] [SULFONYL}-2-METHYLBENZOATE] (404 mg, 1.19 mmol) was suspended in dry [CH2C12] (10 mL) and DMF (10 [. L) UNDER N2.] The solution was treated with oxalyl chloride (Aldrich, 0.192 mL, 2.2 mmol) and stirred while gas evolved. After one hour the excess solvent and oxalyl chloride were evaporated and the resultant residue was taken up in dry [CH2C12] (10 mL). [METHYL-2-AMINO-5-] bromobenzoate (Aldrich, 230 mg, 1.0 mmol) was added as a solution in pyridine (3 mL) and the amber solution stirred at RT. After 2 hours [HPLC] indicated the reaction was complete. The mixture was diluted with CH2Cl2 (100 [ML)] and washed 2x with 1. OM HC1 followed by brine (100 mL each). The organic layer was evaporated and purified on a Biotage Flash 25M+ (40 g) silica cartridge using [CH2C12.] The combined fractions were evaporated and the product was dried under vacuum at [100 C] to afford 535mg (97%) of a glass-like [SOLID. 1H NMR] (400 MHz, DMSO-d6) 8 10.88 (s, 1 H), 8.05 (d, J= 8.9 Hz, [1] H), 7.99 (d, J= 2.3 Hz, 1 H), 7.93 (D, J= 7.5 Hz, 1 H), 7.86 (dd, J= 8.8, 2.4 Hz, 1 H), 7.80 (d, J= 7.3 Hz, 1 H), 7.57 (t, J= 7.9 Hz, 1 H), 7.45 (d, [J=8. 7HZ, 2H),] 7.29 (d, [J=8. 7HZ, 2H),] 3.83 (s, [3H),] 3.24 (s, [3H),] 2. [39] (s, [3 H).] 322 mg of the methyl ester solid was dissolved in hot dioxane (10 mL), and after cooling was treated with 1. OM [LIOH] (1.0 [ML,] 1.0 [MMOL).] After stirring overnight at RT the reaction was complete by [HPLC] and OAMS showed correct [M/Z] for the product. The solvent was evaporated and the residue was poured into 1. OM HC1 (100 mL) to afford a white precipitate. The product was extracted into EtOAc (125 [ML)] and washed 3x with [1.] OM HCl, and lx with brine (100 mL each). The organic layer was dried over [NA2S04,] filtered and evaporated to dryness. The crude product was re- [ CRYSTALLIZEDFROMHOTMEOH/ETOH. THERESULTANTPRODUCTWAS DRIEDAT 100 CUNDER] vacuum to afford 213 mg (68%) of white [CRYSTALS. 1H] NMR (400 MHz, DMSO-d6) [B] 11. [35] (s, 1 H), 8. [39] (d, [J=] 8.9 Hz, 1 H), 8.07 (d, [J=] 2.5 Hz, 1 H), 7.92 (dd, [J=] 8.1, 1. [0 HZ, 1 H),] 7.81-7. 89 (m, 2 H), 7.56 (t, [J= 7. 8 HZ, 1 H),] 7.41-7. 48 (m, 2 H), 7.24- 7.34 (m, 2 H), 3.23 (s, 3 H), 2.39 (s, [3 H).]

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
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10259-22-0, name is Ethyl 3-methoxybenzoate, 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. Computed Properties of C10H12O3

General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a.

The synthetic route of 10259-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maekawa, Hirofumi; Okawara, Hikaru; Murakami, Taro; Tetrahedron Letters; vol. 58; 3; (2017); p. 206 – 209;,
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These common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, 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. COA of Formula: C8H8BrNO2

B. Ethyl-2-Bromo-3-benzenepropanoate To a solution of compound A (18 g, 79 mmol) and dimethylformamide (55 mg, 0.75 mmol) in dichloromethane (160 mL) cooled to 5 C. was added a solution of oxalyl chloride (80 mL, 2M in dichloromethane). After stirring for thirty minutes at 5 C., the solution was warmed to room temperature and stirred for an additional two hours. Ethanol (100 mL, absolute) was added slowly to the solution and after 15 minutes, the mixture was heated to reflux and held there for two hours. The ethanol was removed by distillation and the desired product was isolated by vacuum distillation (107-115 C. at 0.5 mm Hg) as a colorless oil (12.63 g, 49 mmol, 62%).

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

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5225408; (1993); A;,
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Electric Literature of 680-65-9,Some common heterocyclic compound, 680-65-9, name is Diethyl difluoromalonate, molecular formula is C7H10F2O4, 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.

In a dry 25 mL round bottom flask under an Ar atmosphere, NaOEt (9.71 mL, 26.0mmol) in EtOH (21 % weight) and diethyl-2,2-difluoromalonate (2.55 g, 13.0 mmol) werestirred at rt for 10 mm. A solution of Example id (554 mg, 1.30 mmol) in EtOH (6.00mL) was added dropwise and the reaction was stirred at rt over 18 hrs. The EtOH wasremoved in vacuo and the crude oil was dissolved in 1 M HC1 (10 mL). The aqueoussolution was extracted with EtOAc (20 mL x 3), and the combined organics were washedwith aq NaC1 (20 mL), dried over Na2SO4, filtered into a round bottom flask andconcentrated in vacuo to give the title compound as a crude brown oil (749 mg, 1.30mmol). MS (ESI) 576.0 [M+H]+.

The synthetic route of 680-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; BUSCH, Brett, B.; AVERBUJ, Claudia; VALENTE, Meriah; WURTZ, Nicholas; RAO, Prasanna Savanor, Maddu; SHETTY, Jeevanprakash; VENU, Alla; WO2014/152738; (2014); A1;,
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Related Products of 18358-63-9,Some common heterocyclic compound, 18358-63-9, name is Methyl 4-(methylamino)benzoate, molecular formula is C9H11NO2, 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.

Part D: To the mixture of the product from Step C (412.0 mg, 2.5 mmol) and Et3N (0.5 mL) in CH2Cl2 at 0 C. was added chloroacetyl chloride (0.24 mL, 3.0 mmol) and DMAP (15 mg). After stirring at this temperature for 1.5 hr, the reaction mixture was washed with water and brine and dried over MgSO4. The residue was purified by chromatography on silica gel (20% ethyl acetate in hexane) to give the desired product as a white solid. LC/MS ESI found: (M+1)+=242.3.

The synthetic route of 18358-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Han, Wei; Hu, Zilun; Qiao, Jennifer; US2003/232804; (2003); A1;,
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