Tag: M.W=100-200

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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27492-84-8

Synthesis of 4-(2-Chloro-ethylamino)-2-methoxy-benzoic acid methyl ester 16; Methyl 4-amino-2-methoylbenzoate (2 g, 11.04 mmol, 1 eq) was dissolved in methanol (30 ml) and a 1:1 mixture (2 ml) of 6M aq. HCl and methanol was added. Chloroacetaldehyde (50percent in water, 2.08 ml, 13.27 mmol, 1.2 eq) was added and the mixture was cooled to 0° C. NaBH3CN (0.78 g, 12.37 mmol, 1.12 eq) was added in portions over 2 min and the mixture was stirred for 5 days at ambient temperature. The mixture was poured into sat. aq. NaHCO3 (100 ml) and DCM (100 ml) was added, the pH was adjusted to 7-8 with dil. aq. HCl and the organic layer was poured off. The aqueous layer was then extracted with DCM (2.x.50 ml) and the combined organic layers were washed with water (2.x.100 ml), were washed with brine (50 ml), were dried over Na2SO4, filtered and the solvent was removed in vacuo. The product was purified via column chromatography eluted with a gradient from 1:1 to 1:3 CyH:EtOAc (Rf product=0.5, Rf SM=0.35 in 1:3 CyH:EtOAc, UV, KMnO4). This gave 1.968 g (73percent) of white solid. 1H-NMR (CDCl3) 500 MHz: delta (ppm)=3.55 (2H, br.quart, J=5.1 Hz, ClCH2CH2), 3.71 (2H, t, J=5.9 Hz, ClCH2CH2), 3.82 (3H, s, COCH3), 3.86 (3H, s, COOCH3), 4.48 (1H, br.s, ClCH2CH2NH), 6.13 (1H, d, J=1.9 Hz, CCHCN), 6.19 (1H, dd, J=2.0 Hz, J=8.6 Hz, CCHCHCN), 7.77 (1H, d, J=8.6 Hz, CCHCHCN). 13C-NMR (CDCl3) 125 MHz: delta (ppm)=43.1 (CH2), 44.8 (CH2), 51.4 (CH3), 55.8 (CH3), 96.1 (CH), 104.1 (CH), 108.8 (C), 134.3 (CH), 152.2 (C), 161.8 (C), 166.1 (CO). IR Spectrum; evaporated film: v(cm-1)=3361, 2950, 2840, 1700, 1607, 1526, 1346, 1255, 1182, 1085. MS-ES (negative): 242.1 (M-H+), 244.1 (M-H+). MS-ES (positive): 244.1 (M+H+), 246.1 (M+H+).

According to the analysis of related databases, 27492-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Desreumaux, Pierre; Bellinvia, Salvatore; Chavatte, Philippe; Baroni, Sergio; US2011/39808; (2011); A1;,
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These common heterocyclic compound, 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, 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: C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

The synthetic route of Methyl 3-(4-aminophenyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 63485-50-7

Step 1: methyl (trans-3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yI)cyclobutane-l- carboxylate : into a 250-mL round-bottom flask, under nitrogen, was placed a solution of methyl 3-cis-hydroxycyclobutane-l -carboxylate (8 g, 61.47 mmol, 1.00 equiv), 2,3-dihydro- l H-isoindole-l ,3-dione (18.1 g, 123.02 mmol, 2.00 equiv) and triphenylphosphine (32.3 g, 123.15 mmol, 2.00 equiv) in THF (100 mL). This was followed by the addition of D1AD (24.9 g, 123.14 mmol, 2.00 equiv) dropwise with stirring at 0 C. The resulting solution was stirred for 2.5 hours at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :5). The crude product was re-crystallized from petroleum ether/ethyl acetate in the ratio of 10: 1. This resulted in 7.2 g (45%) of methyl trans-3-(l ,3-dioxo-2,3-dihydro-lH-isoindol-2- yl)cyclobutane-l -carboxylate as a white solid. LC-MS (ES, m/z): [M+l ]+ = 260. -NMR (400MHz, CDC13): delta 7.85-7.82 (m, 2H), 7.74-7.71 (m, 2H), 5.08-5.04 (m, 1 H), 3.75 (s, 3H), 3.34-3.32 (m, 1 H), 3.20-3.12 (m, 2H), 2.66-2.60 (m, 2H).

The synthetic route of 63485-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (96 pag.)WO2016/105468; (2016); 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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Formula: C7H10O2

Lithium bis(trimethylsilyl)amide (4.95 mL, 4.95 mmol, 1.0 M in THF, 1.55 equiv.) was cooled to -78 C, then i-butyl propiolate (604 mg, 4.789 mmol, 1.5 equiv.) in 3 mL THF was added and the reaction mixture was stirred for 45 min. The solution was then added via cannula over 10 min to ketone (3R)-9 (953 mg, 3.193 mmol, 1 equiv.) in 5 mL THF at -78 C and stirred for 2 h. The reaction was quenched with satd aq NH4Cl (50 mL), warmed to rt, and extracted with EtOAc (4 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (50%? 100% CH2Cl2 in hexanes) yielded the ester (15,3R)-10 as a clear viscous oil (1.05 g, 78%). IR (ATR): 3400, 2956, 2932, 2888, 2860, 2248, 1710, 1473, 1395, 1371, 1258, 1204, 1153, 1114, 1039, 1013, 909, 888, 838, 781, 751, 732, 695, 672, 657. 1H-NMR (500 MHz; CDCl3): delta 7.63-7.60 (m, 1H), 7.47-7.45 (m, 2H), 7.38-7.37 (m, 1H), 5.19 (dd, 7 = 8.0, 6.3 Hz, 1H), 2.96 (d, 7 = 2.3 Hz, 1H), 1.49 (s, 9H), 0.95 (s, 9H), 0.24 (s, 6H). 13C-NMR (126 MHz; CDCl3): delta 151.8, 139.5, 139.1, 130.9, 130.3, 124.9, 124.4, 124.2, 84.2, 80.6, 78.2, 74.9, 74.4, 28.0, 25.7, 18.2, -4.65, -4.84. 19F-NMR (471 MHz; CDCl3): delta delta -115.05 (d, 7 = 224.7 Hz, 1F), -128.46 (d, 7 = 224.6 Hz, 1F). HRMS (ESI) m/z calcd for C22H30O4F2SiNa ([M+Na]+) 441.1779; found 441.1785.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; TAN, Derek, Shieh; EVANS, Christopher, E.; SHARMA, Indrajeet; TONGE, Peter, James; MATARLO, Joe, S.; (242 pag.)WO2017/59411; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5445-17-0, name is Methyl 2-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 5445-17-0, Safety of Methyl 2-bromopropanoate

tert-Butyl 5<;hloro-3-(1 -methoxycarbonylethyl)-2<>xo-2,3Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); 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. 40061-54-9, name is Ethyl 2-(2-chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-(2-chlorophenyl)acetate

o-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl o-chlorophenylacetate was obtained by column chromatography, in a yield of 83percent. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.77 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 7.21-7.24 (m, 2H), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 39.2, 61.0, 126.9, 128.6, 129.5, 131.4, 132.6, 134.6, 170.6; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0343. The ethyl o-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 66 mg product o-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent.

The synthetic route of 40061-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C9H16O3

A 250-mE 3-necked round-bottom flask fitted with a magnetic stir bar and thermometer was charged with ethyl 4-hydroxycyclohexane-i -carboxylate (1.5 g, 8.71 mmol), tnethylamine (2.64 g, 26.09 mmol) and dichloromethane (50 mE). To the reaction was added methanesulfonyl chloride (1.49 g, 13.01 mmol) added dropwise with stirring at 00 C. The resulting solution was stirred for 2 h at 25° C. The resulting solution was diluted with water (20 mE) and the product was extracted with dichloromethane (3×20 mE). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:5, v/v) to afford ethyl 4-(methane- sulfonyloxy) cyclohexane- 1 -carboxylate as a light yellow oil (1.2 g, 55percent). ECMS: (ESI) mlz 251 [M+H], 155 [M-OMs].

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; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); A1;,
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Electric Literature of 4224-69-5, These common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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 solution of aldehyde 8 (13.0 g, 25 mmol) in THF (80mL) was mixed with saturated solution of NH4Cl (100 mL)and Zn dust (1.6 g, 50 mmol) at the room temperature. Themixture was stirred and the methyl 2-(bromomethyl)acrylate (7.2 g, 40 mmol) was added inseveral portions. The mixture was stirred for 1 hour, diluted with diethyl ether (900 mL), washedby brine (2×150 mL) and dried over Na2SO4. The solvents were evaporated and the product waspurified by column chromatography (EtOAc:hexane 1:2) to obtain 9 (13.4 g, 87%) as a colorlessliquid, diastereomeric mixture (~0.43:0.54 labeled as A and B).

Statistics shows that Methyl 2-(bromomethyl)acrylate is playing an increasingly important role. we look forward to future research findings about 4224-69-5.

Reference:
Article; Baranov, Mikhail S.; Kaskova, Zinaida M.; Grit?enko, Roman; Postikova, Svetlana G.; Ivashkin, Pavel E.; Kislukhin, Alexander A.; Moskvin, Dmitrii I.; Mineev, Konstantin S.; Arseniev, Alexander S.; Labas, Yulii A.; Yampolsky, Ilia V.; Synlett; vol. 28; 5; (2017); p. 583 – 588;,
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Electric Literature of 7270-63-5,Some common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H6N2O4, 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: 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. 4.2.10. 2,4-Bis(3-fluorophenyl)-6H-furo[2,3-b]pyran-6-one (5i). Reaction of 1 (85 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (132 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5i (69 mg, 43%) as a solid: mp 128-130 C; 1H NMR (300 MHz, CDCl3) delta 7.39-7.37 (3H, m), 7.34-7.27 (3H, m), 7.20-7.18 (1H, m), 6.99-6.96 (1H, m), 6.84 (1H, s), 6.18 (1H, s); 13C NMR (75 MHz, CDCl3) delta 164.6, 161.4, 159.0, 158.9, 152.3, 147.4, 137.0, 136.9, 131.1, 130.7, 123.3, 119.3, 117.9, 115.4, 114.7, 110.7, 105.6, 101.6, 99.4; IR (KBr) 2928, 1761, 1715, 1588, 1437, 1240, 1181, 1076, 926, 784, 692 cm-1; HRMS m/z (M+) calcd for C19H10F2O3: 324.0598. Found: 324.0599.

The synthetic route of 7270-63-5 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;,
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Synthetic Route of 4891-38-7,Some common heterocyclic compound, 4891-38-7, name is Methyl Phenylpropiolate, molecular formula is C10H8O2, 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 of N-methylprop-2-yn-1-amine (1c, 1.5 mmol, 103.6 mg), dimethyl acetylenedicarboxylate (2a, 1.0 mmol, 142.1 mg), AgOAc (16.7mg, 0.1 mmol) and DBU (15 2mg, 1.0 mmol) in DMF (7 mL) in a thick-walled screw-capped Pyrex tube was stirred with a magnetic stirrer at 80 C for 2 h. After cooling to room temperature, the reaction mixture was diluted with saturated aq. NH4Cl (10 mL) and extracted with ethyl acetate (5×10.0 mL). The combined organic phrase was washed with brine (2×15.0 mL) and dried over anhydrous Na2SO4. After removal of solvent under reduced pressure, purification was performed by flash column chromatography on silica gel with petroleum ether/ethyl acetate (7:3) as eluent to afford 4ca in 84 % yield (177. 2mg, 0.84 mmol).

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

Reference:
Article; Nizami, Tauqir A.; Hua, Ruimao; Tetrahedron; vol. 73; 42; (2017); p. 6080 – 6084;,
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