Tag: M.W=100-200

These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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. Quality Control of Methyl 4-amino-2-methoxybenzoate

Example 286; Preparation of rac 4-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-2-methoxy-benzoic acid methyl ester To a stirred solution of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (100 mg, 0.17 mmol) in methylene chloride (10 mL), HATU (Aldrich,118 mg, 0.31 mmol) was added followed by the addition of DIPEA(0.15 mL, 0.86 mmol) and 4-amino-2-methoxy-benzoic acid (Avocado, 62 mg, 0.34 mmol). The mixture was stirred at rt for overnight. The reaction was quenched with addition of water. The mixture was extracted with methylene chloride (2.x.10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on an ISCO machine (40 g column, 5-15percent EtOAc/methylene chloride) to give a white solid. 29 mg.MS (ES+) m/z Calcd: [(M+H)+]: 630.1733, found: 630.1732

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

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Liu, Jin-Jun; Ross, Tina Morgan; Zhang, Jing; Zhang, Zhuming; US2010/75948; (2010); A1;,
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Application of 18595-17-0, A common heterocyclic compound, 18595-17-0, name is Methyl 2-amino-4-methylbenzoate, molecular formula is C9H11NO2, 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.

REFERENCE EXAMPLE 25 Methanesulphonyl chloride (12.2 ml) was added to a stirred, cooled solution of methyl 2-amino-4-methylbenzoate (103 g) and triethylamine (19.5 ml) in dichlorotuethane while maintaining the temperatare below 0 C. The mixture was stirred at room temperature for 4 hours. Hydrochloric acid solution (2M) was added and the layers were separated. The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give a mixture of methyl 4-methyl-2-[N,N-bis(methylsulphonyl)amino]benzoate and methyl 4-methyl-2-(N-methylsulphonylamino)benzoate (18.26 g) as a yellow solid which was not further purified.

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; Rhone-Poulenc Argriculture Limited; US5658858; (1997); A;,
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Reference of 4341-76-8, 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. 4341-76-8, name is Ethyl 2-butynoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 2-aminopyridine (0.1mmol), alkynoate (0.1mmol) and AgSO3CF3 (30mol%) in chlorobenzene (0.8mL) was stirred at 120C for 24h. After the reaction was finished, water (5mL) was added and the solution was extracted with ethyl acetate (3×5mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.

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

Reference:
Article; Chen, Zhengwang; Wen, Yuelu; Ding, Hao; Luo, Guotian; Ye, Min; Liu, Liangxian; Xue, Jun; Tetrahedron Letters; vol. 58; 1; (2017); p. 13 – 16;,
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Some common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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. SDS of cas: 61367-07-5

To a stirred solution of 25 (Nicolaou et al, 2016) (100 mg, 250 pmol, 1.0 equiv) in dry DMF (2 mL) at 0 C were added HATU (285 mg, 750 pmol, 3.0 equiv) followed by Et3N (200 pL, 1.50 mmol, 6.0 equiv) and the resulting mixture was stirred for 5 min at the same temperature. A solution of 26 (59.0 mg, 370 pmol, 1.5 equiv) in dry DMF (0.5 mL) was then added and the stirring was continued for 18 h while allowing the temperature to slowly rise to 23 C. The reaction mixture was diluted with H20 (5 mL) and the resulting solution was extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with brine (5 mL), dried over Na SCL and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (silica gel, 10 50% EtOAc in hexanes) to furnish 27 (113 mg, 210 pmol, 84% yield) as a white amorphous solid. 27: Rf= 0.50 (silica gel, 50% EtOAc in hexanes); [OC]D =-3.6 (c= 1.0, CHC13); FT-IR (film) VmaX: 2936, 1735, 1687, 1663, 1540, 1492, 1368, 1220, 1154, 1130, 1040, 771, 732 cnT1. NMR: (CDC13, 600 MHz) d 8.02 (d, = 2.1Hz, 1H), 7.12-7.01 (m, 1H), 5.82 (dd, J = 11.6, 2.9 Hz, 1H), 4.14-3.84 (m, 2H), 3.67 (d, = 1.5 Hz, 3 H), 2.71 (s, 3 H), 2.35-2.20 (m, 2H), 2.15 (s, 2H), 2.15-2.11 (m, 3 H), 2.10-1.98 (m, 3 H), 1.62 (d, = 15.2 Hz, 2H), 1.44 (s, 9H), 1.37- 1.22 (m, 3 H), 0.98-0.96 (m, 3 H), 0.86 (ap. d, J= 2.9 Hz, 3 H) ppm; 13C NMR: (CDC13, 150 MHz) d 175.7, 170.4, 160.0, 150.1, 139.7, 128.2, 123.3, 79.4, 69.2, 56.4, 51.6, 48.4, 47.7, 42.4, 35.0, 32.1, 31.9, 30.4, 28.3, 27.8, 20.9, 20.0, 19.5; Diagnostic signals of minor rotamer. 13C NMR: (CDCI3, 150 MHz) d 175.6, 170.1, 156.3, 150.3, 142.4, 131.0, 123.1, 79.8, 70.9, 51.6, 47.4, 42.3, 35.4, 32.0, 31.7, 30.5, 28.4, 27.8, 21.0, 19.7 ppm; HRMS calcd for C26H4iN307SNa+ [M+Na]+ 562.2563 found 562.2572.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61367-07-5, its application will become more common.

Reference:
Patent; WILLIAM MARCH RICE UNIVERSITY; NICOLAOU, Kyriacos, C.; ERANDE, Rohan, Diliprao; VOURLOUMIS, Dionisios; PULUKURI, Kiran, Kumar; RIGOL, Stephan; (262 pag.)WO2019/108685; (2019); A1;,
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Synthetic Route of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

The 17.4g (94.9mmol) 3-amino-4-fluoro-benzoic acid ethyl ester (reference L.S.Fosdick, A.F.Dodds, J.Amer Chem.Soc. 65,2305 (1943)) and 9.67 ml (11.47g, 105 . 4mmol) methoxy acetyl chloride then 310 ml of chlorobenzene to the solution in the 50 C stirring 2 hours, then reflux 30 minutes. Concentrated under reduced pressure to dryness, purified by silica gel column chromatography (dichloromethane/ethanol = 100:1), oily product to be 3-amino-4-fluoro-benzoic acid ethyl ester, after a few days is cured into a solid (20.1g, yield 83%). R f value: 0.38 (silica gel: dichloromethane/ethanol = 19:1). Mass spectrometric (ESI-MS): 256.1(M+H) +, 278.1(M+Na) +; C 12 H 14 FNO 4 (255).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xizang Hai Sike Pharmaceutical Group Co., Ltd.; Li Qilin; Li Yue; Dang Juan; Long Yu; (53 pag.)CN103524559; (2016); B;,
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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. 40637-56-7, name is Dimethyl 2-allylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Dimethyl 2-allylmalonate

A typical procedure for the iodine(III) reagent-induced anti-Markovnikov hydroazidation of unactivated alkenes: to asolution of 4-phenyl-1-butene (1a) (0.030 mL, 0.2 mmol)and ABX-N3 (11.6 mg, 0.04 mmol) in dichloromethane(DCM) (0.2 mL), TMSN3 (0.052 mL, 0.4 mmol) and HOAc(0.024 mL, 0.4 mmol) were added under an argon atmosphereat room temperature. The reaction mixture was thenstirred for 4 h and monitored by thin layer chromatography(TLC) until 1a was completely consumed. After that, theaqueous of NaOH was added to quench extra HN3 [18], andthe mixture was extracted by Et2O for two times. The organiclayer was dried over MgSO4, filtered and concentrated undervacuum. The residue was purified by flash column chromatography(petroleum ether/ethyl acetate, 20:1 to 10:1) togive product 2a in 83% yield.

The synthetic route of 40637-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Xiaonan; Chen, Pinhong; Liu, Guosheng; Science China Chemistry; vol. 62; 11; (2019); p. 1537 – 1541;,
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Some common heterocyclic compound, 110-42-9, name is Methyl decanoate, molecular formula is C11H22O2, 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. SDS of cas: 110-42-9

General procedure: The succinic Gemini surfactants, dl- and meso-2,3-bis(alkyl)succinic acids, were synthesized by the oxidative coupling of enolates of fatty acid esters with copper(II) bromide according to Quermann et al. [35] and subsequent deprotection of ester groups. Following is a typical synthesis of di-tert-butyl 2,3-bis(undecyl)succinate, 2e: first of all, tert-butyl tridecanoate 1e was prepared from tert-butanol, tridecanoic acid, dicyclohexyl carbodiimide (DCC) and DMAP (0.2 equiv) in toluene under stirring at room temperature. In a dry 100 mL flask equipped with a dropping funnel, septum inlet, and magnetic stirrer, a solution of 12.5 mL of lithium diisopropylamide (2.0 M in hexane/THF) and 30 mL of dry THF were added under nitrogen. Under cooling at -78 C, 25 mmol of 1e in 10 mL dry THF was added dropwise over a period of 30 min, and then the mixture was stirred for an additional 15 min. With vigorous stirring 5.0 g of anhydrous CuBr2 powder was added all at once to the solution. After stirring for 30 min, the reaction was quenched by adding 50 mL of 1 M HCl at this temperature, and the mixture was allowed to reach room temperature. After extracting twice with hexane (75 mL each), the combined organic layer was washed with water and dried over Na2SO4. By means of a short path vacuum distillation apparatus, both unreacted ester and alpha-bromo ester (5e) were distilled off (*160 C,1 mmHg). The residue was subjected to column chromatography on silica eluting with hexane/diethyl ether(20:1) to separate dl- (dl-2e) and meso-isomers (meso-2e) at the yields of 36 and 25 %, respectively. Other dl- and meso-isomers of 2a-2g were also prepared in a similar manner, and diastereomers (dl and meso) were separated by SiO2 chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110-42-9, its application will become more common.

Reference:
Article; Kawase, Tokuzo; Kagawa-Ohara, Maiko; Aisaka, Tsunetomo; Oida, Tatsuo; Journal of Surfactants and Detergents; vol. 18; 4; (2015); p. 615 – 627;,
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Adding a certain compound to certain chemical reactions, such as: 7335-27-5, name is Ethyl 4-chlorobenzoate, 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 7335-27-5, Product Details of 7335-27-5

General procedure: A mixture of benzoic acid (6.42 mmol), catalytic quantity of conc. H2SO4 in ethanol was heated to reflux for 10 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was washed with saturated NaHCO3 followed by water and brine solution. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain respective ethyl benzoates. To a stirred solution of ethyl benzoates (5 mmol) in ethanol was added hydrazine-hydrate (12.5 mmol) and refluxed for 8 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain respective benzohydrazides 7a-k.

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Reference:
Article; Saidugari, Swamy; Rao, V. Lakshmana; Vidya; Ram; Balram; Asian Journal of Chemistry; vol. 28; 3; (2016); p. 639 – 643;,
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Adding a certain compound to certain chemical reactions, such as: 6290-49-9, name is Methyl 2-methoxyacetate, 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 6290-49-9, Formula: C4H8O3

A solution of methyl 2-methoxyacetate (2.82 g, 27.10 mmol), NBS (5.04 g, 28.33 mmol) and AIBN (0.081 g, 0.49 mmol) in trifluoromethylbenzene (50 mL) was stirred at 80C for 5 hr. The reaction solution was cooled, and the precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to give an oil. The obtained oil was added to a solution of N-benzyl-2-(3-methoxyphenoxy)ethanamine (6.34 g, 24.64 mmol) and DIEA (5.15 mL, 29.57 mmol) in THF (60 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was added to aqueous sodium hydrogen carbonate solution, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 2?20% ethyl acetate/hexane) to give methyl 2-(benzyl(2-(3-methoxyphenoxy)ethyl)amino)-2-methoxyacetate (6.72 g, 18.70 mmol, 76%) as a colorless oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); 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. 6290-49-9, name is Methyl 2-methoxyacetate, A new synthetic method of this compound is introduced below., COA of Formula: C4H8O3

General procedure: To a distilled benzene solu-tion (50 mL) of methyl 2-methoxyacetate (5.2 g, 50 mmol) wereadded a magnetic stirring bar and N-bromosuccinimide (8.9 g,50 mmol), and the mixture was stirred at room temperature for 1 hunder irradiation of a sunlight lamp. The reaction mixture was l-tered, and then evaporated under reduced pressure. The residuewas dissolved in THF (50 mL) containing sec-amine (60 mmol) andtriethylamine (6.1 g, 60 mmol), and the mixture was stirred for 2 hat room temperature. The mixture was directly ltered withouta common workup and was evaporated under reduced pressure.The ltrate was distilled (a Kugelrohr distillation) to give the N,O-acetal 2. 4.1.1.4. Methyl 2-(diallylamino)-2-methoxyacetate16d(2d). 75%yield (7.47 g); colorless oil;1H NMR (300 MHz, CDCl3) d 3.26e3.36(m, 7H), 3.77 (s, 3H), 4.46 (s, 1H), 5.13e5.24 (m, 4H), 5.80 (m, 2H);13C NMR (75 MHz, CDCl3) d 51.8, 52.1, 55.5, 89.7, 117.5, 135.7, 169.8;MS (ESI): m/z 222 [MNa]; HRMS (ESI): Calcd for C10H17NNaO3:222.1106, found: 222.1095.

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; Sakai, Norio; Hori, Hiroaki; Yoshida, Yoshihiro; Konakahara, Takeo; Ogiwara, Yohei; Tetrahedron; vol. 71; 29; (2015); p. 4722 – 4729;,
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