Month: September 2021

These common heterocyclic compound, 29823-21-0, name is Ethyl 8-Bromooctanoate, 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: C10H19BrO2

General procedure: 2,6-dichloro-9H-purine (5 mmol) or intermediates 5 was dissolved in 20 mL anhydrous DMF, then K2CO3 (8 mmol) was added, and ethyl 4-bromobutanoate or ethyl 8-bromooctanoate(8 mmol) was dropped into the solution. Cut off from the air, the solution was stirred at room temperature for overnight,and then adjusted to pH 7-8 with HCl (1 mol/L), then extracted with 50 mL ×3 ethyl acetate and the organic phase was combined, and washed with brine, dried over MgSO4 and evaporated. The crude product was purified by chromatography on a silica gel column (EtOAc/petroleum ether, 1 : 1) to give desired compounds 6a-6p.

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

Reference:
Article; Xu, Zhaoxing; Yang, Yongchao; Mai, Xi; Liu, Bin; Xiong, Yuanzhen; Feng, Lihuang; Liao, Yijing; Zhang, Yu; Wang, Huanlu; Ouyang, Leiting; Liu, Shuhao; Chemical and Pharmaceutical Bulletin; vol. 66; 4; (2018); p. 439 – 451;,
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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. 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, A new synthetic method of this compound is introduced below., COA of Formula: C8H10O5

General procedure: To a round bottomed flask equipped with a magnetic bar, benzaldehyde 2a (200 mg, 1.15 mmol) and freshly prepared benzoyl Meldrum?s acid 4a (430 mg, 1.73 mmol) were added in 2 mL THF-H2O (5:1). Then the catalyst DMEDA (25 mL, 0.23 mmol) was added and the reaction mixture was allowed to stir for 12 h at 55 C. After the complete consumption of benzaldehyde 2a (monitored by TLC), reaction mixture was filtered through anhydrous Na2SO4 and the residue was purified by column chromatography over silica gel using ethyl acetate in petroleum ether as eluent. The product 5a was obtained as pale yellow viscous oil in 82% yield (261 mg).

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:
Article; Khopade, Tushar M.; Warghude, Prakash K.; Mete, Trimbak B.; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 60; 2; (2019); p. 197 – 200;,
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Electric Literature of 252881-74-6, A common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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 25 mg of 3-(3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acid 8.1, 12 mg of tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, and 17.8 mg of diisopropylethylamine in 1 mL of DMF was treated with 15 mg of HATU. The mixture was stirred for 1 h and then the product was isolated by reverse phase HPLC eluting with 0.05% TFA in a water/acetonitrile gradient.

The synthetic route of 252881-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
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Electric Literature of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 2: l-(2-(Benzyloxy)ethyl)-4-(/- butyldimethylsilyloxy)cyclohexanecarbaldehyde; Step a: Ethyl 4-(tert-butyldimethylsilyloxy)cyclohexanecarboxylate; [00164] A mixture of ethyl 4-hydroxycyclohexane-carboxylate (50 mL, 0.31mol), imidazole (50.1 g, 0.74 mol), and t-butyldimethylsilyl chloride (56 g, 0.37mol) in DMF (580 mL) was stirred at room temperature for 20 hrs under atmosphere of nitrogen. Water (100 mL) was added to the mixture, and the mixture was extracted with ether (600 mL). The extract was washed with water (400 mL) and brine (500 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give compound 2 as a colorless oil (102 g), which was used for the next step without further purification.

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

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, 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 15963-40-3, Application In Synthesis of Methyl 3-methylenecyclobutanecarboxylate

To a methyl acetate (45 mL) solution of methyl 3-methylenecyclobutanecarboxylate (Intermediate 43A) was added copper powder (2.77 g, 43.6 mmol) and zinc powder (5.70 g, 87 mmol). To this mixture was added a methyl acetate (45 mL) solution of 2,2,2-trichloroacetyl chloride (4.86 mL, 43.6 mmol) and phosphorus oxychloride (0.37 mL, 4.0 mmol) dropwise over 2 h. After 3 h, the reaction was cooled to 0 C, and additional zinc powder (5.70 g, 87 mmol) was added, followed by acetic acid (22.7 mL, 400 mmol) dropwise at a rate keeping the temperature below 7 C. The reaction was allowed to slowly warm to room temperature and after stirring overnight was filtered through Celite, rinsing with EtOAc. The filtrate was carefully washed (warning: gas evolution) with saturated aqueous NaHC03 (2 X 200 mL), and the aqueous layers extracted with 1 :1 EtOAc:Et20 (2 X 100 mL). The combined organic layers were dried over MgS04, filtered and concentrated, and the residue purified on silica gel eluting with a 0%-50% EtOAc-hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (4.10 g, 61 %) as a yellow oil. 1H NMR (400 MHz, CDCI3) delta 2.38-2.48 (m, 2 H), 2.50-2.61 (m, 2 H), 3.00- 3.09 (m, 2 H), 3.09-3.22 (m, 3 H), 3.68 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-methylenecyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 3-(4-aminophenyl)acrylate

Example 11: (2E)-3-{4-[({l-[({14-[(trans)-2-fluorocyclohexyl]-6-isopropyl-3-methoxy-5,6,7,8- tctrahydroindolo[2,l -a] [2,5]bcnzodiazocin-l 1 -yl}carbonyl)amino] cyclopcntyl} carbonyl)amino]phcnyl}acrylic acid Step 1: ethyl (2E)-3-(4-{f(l-aminocvclopentyl)carbonylJamino}phenyl)acrylate trifluoroacetate l-{[(benzyloxy)carbonyl]amino}cyclopentanecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq) and triethylamine (3 eq) were added, followed by ethyl (2u)-3-(4-aminophenyl)acrylate (0.95 eq). The resulting mixture was stirred for 48 h at 40 0C. DMF was evaporated, the resulting oil taken up in EtOAc and the solution washed with aqueous HCl (IN), water, saturated aqueous NaHCO3 and brine. Drying over NaHSO4 and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1, containing 1percent EtOH) as the eluent. The resulting solid was dissolved at 0 0C with a 1 : 1 mixture of TFA:CH2C12, and the solution (0.1 M) was stirred for 2 h at RT. Evaporation gave a residue that was triturated with toluene to afford a solid that was used without further purification in the subsequent step. 1H NMR (400 MHz, DMSO-fi?6, 300 K) delta, 1.34 (t, J 6.9, 3H), 1.90- 2.12 (m, 4H), 2.50-2.65 (m, 4H), 4.15 (q, J6.9, 2H), 6.62 (d, J 16.0, 1 H), 7.69 (d, J 16.0, 1 H), 7.80 (br s, 2H), 8.35 (br s, 2H) 10.22 (s, IH); MS (ES+) m/z 303 (M+H)+.

The synthetic route of 5048-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/54741; (2007); A1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 454-31-9, 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. 454-31-9, name is Ethyl 2,2-difluoroacetate, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of LiAlH4 in THF ( (97%, 3.96 g, 101.2 mmol, 200 mL) was addedethyl 2,2-difluoroacetate (24.76 g, 199.5 mmol) dropwise at -10 C. After addition, the reactionmixture was continued to stir for 1 h, then adjusted to pH= 2~3 with 2 M HCl solution. The resulting mixture was distilled and collected distillation at 90~96 oc to give the title compoundas colorless oil (7.30 g, yield 44.6%).1H NMR (400MHz, CDCb) 8 (ppm): 5.85 (tt, J = 55.7, 3.8 Hz, 1H), 3.81 (td, J = 14.5, 3.8 Hz,2H);19F NMR (376 MHz, CDCb) 8 (ppm): -127.90.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2,2-difluoroacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; DAI, Weilong; XI, Ning; LI, Minxiong; ZHANG, Tao; LI, Xiaobo; HU, Haiyang; CHEN, Wuhong; WANG, Tingjin; LIU, Jun; (188 pag.)WO2017/48675; (2017); A1;,
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Electric Literature of 5616-81-9, 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. 5616-81-9 name is tert-Butyl 2-(methylamino)acetate, 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.

To a solution of alkylaminosulphonylphenylmethyl bromide (50 mg, 0.142 mmol) in DMF (5 mL) was added tert-butyl sarcosine (75 mg, 0.4 mmol) and cesium carbonate (100 mg, 0.28 mmol). The reaction was allowed to stir at room temperature overnight before it was poured into water and extracted with CH2CL2. The organic layer was washed with brine, dried over MGS04 and the solvent was removed in vacuo. Eluting through a solid phase extraction tube (5G) with 5% ethyl acetate/hexanes afforded the product (21 mg, 36%) 1H-NMR (CDC13) 8 : 7.93 (s, 1H) 7.52 (d, 1H), 7.47 (d, 1H) 3.88 (s, 2H), 3.24 (s, 2H), 2.99 (t, 4H), 2.42 (s, 3H), 1.53-1. 61 (m, 4H), 1.45 (s, 9H), 1.39-1. 42 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 2-(methylamino)acetate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA; NPS PHARMACEUTICALS, INC.; WO2004/92135; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 61644-18-6, 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. 61644-18-6, name is Chloromethyl isobutyrate, This compound has unique chemical properties. The synthetic route is as follows.

A 1-L jacketed glass reactor equipped with a nitrogen pad, overhead stirrer motor, down-pumping 45 pitched 4-blade impeller, “h” baffle, West condenser, and thermowell was charged sequentially with solid UK-2A (56.10 g, 0.109 mol, 1.0 equiv), anhydrous Na2C03(23.09 g, 0.218 mol, 2.0 equiv), solid Nal (0.979 g, 0.0065 mol, 6 mol%), nonyl phenyl ketone (1.5022 g, nonreactive internal standard for HPLC analysis), 15-crown-5 (2.444 g, 0.0109 mol, 10 mol%), neat chloromethyl isobutyrate (16.47 g, 0.120 mol, 1.1 equiv), and ethyl acetate (361 g). The 1-L reactor was placed under an atmosphere of nitrogen, agitation was initiated, and the reaction mixture was heated to 65 C. Samples of the reaction mixture (approximately 1 mL) were removed at 5 h and 10 h. Each sample was added to fresh ethyl acetate (5 mL), syringe filtered, and diluted approximately 6: 1 (v/v) with 0.1% formic acid in N,N-dimethylformamide. The resulting samples were analyzed by HPLC (UV detection, 270 nm) and the molar concentrations of unreacted UK-2A (Formula IV), Formula (VI), and the by-product of Formula (VII) were determined based on the known quantity of internal standard (nonyl phenyl ketone). The conversion of Formula (IV) and the yields of Formula (VI) and Formula (VII) could be calculated on the basis of this information (see for example Entry 4 of Table 1).

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

Reference:
Patent; DOW AGROSCIENCES LLC; JANSMA, Matthew; ADAWAY, Timothy; TRIPPEER, Michael; (19 pag.)WO2017/62362; (2017); 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. 403-33-8, name is Methyl 4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 4-fluorobenzoate

Example 7; Methyl 9-(3,5-dichloro-4-pyridylcarbamoyl)-6-methoxydibenzo[6,«f]furan-2- carboxylate; Step 1: Methyl-(4-fluoro-3-Bromo) benzoate; EPO Methyl-(4-fluoro) benzoate (28 g, 181.81 mmoles) was added to mixture sulphuric acid (93.63 ml) and water (1.6 ml) then bromine (8.4 ml, 163.63 mmoles) was added at O0C followed by addition of silver sulphate (51.02 g, 163.63 mmoles) .Reaction was stirred for 24 h. at room temperature. Reaction mass was poured in ice cold water (250 ml) and extracted with diethyl ether ( 100 x 3 ml) , dried and concentrated under reduced pressure to yield pale yellow liquid (36 g).1H nmr (300 MHz, DMSOd6): delta 3.86 (s, 3H), 7.54 (t, IH), 7.98-8.04 (m, IH), 8.19- 8.22 (dd, IH, J= 6.6 Hz).IR(KBr) cm4: 3098, 3052, 2847, 1727, 1599, 1507, 1492, 1436, 1389, 1282, 1226, 1107, 1048, 860, 763, 608.

The synthetic route of 403-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; KHAIRATKAR-JOSHI, Neelima; WO2006/51390; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics