Tag: M.W=100-200

A common heterocyclic compound, 13671-00-6, name is Methyl 2,6-difluorobenzoate, molecular formula is C8H6F2O2, 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. 13671-00-6.

Step 3: methyl 2,6-difluoro-3-nitrobenzoateTo a solution of methyl 2,6-difluorobenzoate (68.8 g, 0.4 mol) in con. H2SO4 (300 mL) was added potassium nitroperoxous acid (48.5 g, 0.48 mol) for three times and the resulting reaction mixture was stirred at room temperature for 2 hrs. The mixture was droped into ice-water (500 mL) and filtered. The solid was washed with water and dried to afford the desired product (89 g, 100%).1H NMR (DMSC i): ? 8.49-8.43 (1H, m), 7.56-7.51 (1H, m), 3.95 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,6-difluorobenzoate, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; LI, Jijun; ZHU, Yan; HU, Yuandong; WANG, Huting; WANG, Zhe; WANG, Zanping; WEI, Yongheng; SUN, Yinghui; WU, Qiong; ZHANG, Hui; PENG, Yong; KONG, Fansheng; SUN, Ying; LUO, Hong; HAN, Yongxin; WO2013/71865; (2013); A1;,
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42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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 round bottom flask was charged with S11 (10.0 g, 0.056 mol, 1.0 equiv.), tert-butyl methylmalonate (12.3 ml, 0.074 mol, 1.3 equiv.), (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidi-ne (3.7 g, 0.011 mol, 0.2 equiv.), and 100 mL of EtOH. The reaction mixture was stirred atroom temperature for 16 h and was then concentrated in vacuo. Purification of the crudeproduct by flash chromatography on silica gel (petroleum ether:EtOAc, 5:1 v/v) afforded S2as a pair of diastereoisomers (15.1 g, 76percent), both as yellow oil.S2-upper: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.30; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.81 (d,J = 8.8 Hz, 1H), 7.55 (t, J = 7.2 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.39 (t, J = 8.4 Hz, 1H), 4.56 ? 4.50 (m, 1H),3.83 (d, J = 9.2 Hz, 1H), 3.57 (s, 3H), 3.12 ? 2.97 (m, 2H), 1.43 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 199.6,167.9, 166.5, 150.3, 134.8, 132.8, 129.3, 128.2, 124.7, 83.2, 57.2, 52.6, 46.6, 33.7, 27.8, 27.8, 27.8; IR (neat): vmax= 1727, 1355, 845, 749 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7, 374.1210; found 374.1210; [alpha]D25= +63.4 (c 0.20, MeOH).S2-lower: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.26; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.82 (d,J = 8.4 Hz, 1H), 7.55 (t, J = 8 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.38 (t, J = 7.6 Hz, 1H), 4.53 ? 4.47 (m, 1H), 3.87(d, J = 9.6 Hz, 1H), 3.73 (s, 3H), 3.08 ? 2.94 (m, 2H), 1.20 (s, 9H); 13C NMR (100MHz, CDCl3): delta 199.6, 168.4,165.9, 150.2, 135.0, 132.9, 129.5, 128.2, 124.7, 82.8, 57.1, 52.7, 47.3, 34.1, 27.4, 27.4, 27.4; IR (neat): vmax =1727, 1529, 844, 787 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7 374.1210; found 374.1210; [alpha]D25 =+32.5 (c 0.30, MeOH).

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

Reference:
Article; Wang, Xiaobei; Xia, Dongliang; Qin, Wenfang; Zhou, Ruijie; Zhou, Xiaohan; Zhou, Qilong; Liu, Wentao; Dai, Xiang; Wang, Huijing; Wang, Shuqing; Tan, Ling; Zhang, Dan; Song, Hao; Liu, Xiao-Yu; Qin, Yong; Chem; vol. 2; 6; (2017); p. 803 – 816;,
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2005-10-9, The chemical industry reduces the impact on the environment during synthesis 2005-10-9, name is 6H-Benzo[c]chromen-6-one, I believe this compound will play a more active role in future production and life.

2a (58.8 mg, 0.3 mmol), NaBH4 (17.1 mg, 0.45 mmol) and EtOH (3 mL) was added to a flask (10 mL) and stired for 6 h at room temperature. The reaction mixture was wished with CH2Cl2 (3 x5 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (10/1, V/V) as eluent to give pure 6. 4.4.1. 6H-benzo[c]chromen (6)Prepared from 6H-benzo[c]chromen-6-one; isolated as whitesolid (50.3 mg, 92%), m.p. 130-132 C; 1H NMR (500 MHz, CDCl3):d 7.52-7.50 (m, 1H), 7.42-7.40 (m, 2H), 7.29-7.26 (m, 2H), 7.12 (dd,J1 7.5 Hz, J2 1.5 Hz, 1H), 7.02-6.99 (m, 1H), 6.95 (d, J 8.5 Hz,1H), 4.48e4.42 (m, 2H); 13C NMR (125 MHz, CDCl3): d 152.9, 138.9,136.5,130.9,130.8,129.4,129.3,128.6,128.5,127.8,120.8,116.4, 63.7.

The chemical industry reduces the impact on the environment during synthesis 6H-Benzo[c]chromen-6-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui; Tetrahedron; vol. 73; 2; (2017); p. 154 – 163;,
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Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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. 4224-69-5

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4224-69-5, its application will become more common.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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4224-69-5,Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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 mixture of methyl 2-(bromomethyl)acrylate (239 mul, 2 mmol) in petroleum ether (3 ml) was added potassium carbonate (276 mg, 2 mmol), followed by sodium methoxide (119 mg, 2.2 mmol) and methanol (450 mul). The resulting mixture was stirred overnight, filtered, concentrated to a residue that was purified by column chromatography eluting with 10% ether in hexanes to provide the title compound (150 mg, 58%). (Reference: J. Med.Chem.; 42; 15; 1999; 2760-2773.)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(bromomethyl)acrylate, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
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25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 mixture of 4.203 g (25 mmol) of ethyl 4,4,4-trifluorocrotonate, 20 mL of nitromethane and ca. 0.576 g (5 mmol) of tetramethyl guanidine was stirred for 13 hours at room temperature, and then diluted with water and acidified by the addition of 0.5 M sulfuric acid. The mixture was extracted three times with diethyl ether. The combined ether extracts were washed with water, and then brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5.601 g (98%) of 4,4,4-trifluoro-3-nitromethyl-butyric acid ethyl ester as an amber oil.

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 25597-16-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Zhi; ERICKSON, Shawn David; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/60341; (2014); A1;,
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455-68-5, A common heterocyclic compound, 455-68-5, name is Methyl 3-fluorobenzoate, molecular formula is C8H7FO2, 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.

General procedure: The oil was thendissolved in EtOH, and NH2NH2.H2O (3 eq) was added.The mixture was refluxed for 10 h. CH2Cl2 (30 mL) was thenadded and extracted with distilled H2O (3 ¡Á 20 mL). Theorganic phase was separated, dried on anhydrous Na2SO4,and evaporated under vacuum to afford correspondinghydrazide 7a in very good yield (white solid, 1.02g, 93percent)

The synthetic route of 455-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vu, Vu Van; Nhung, Trinh Thi; Thanh, Nguyen Thi; Chinh, Luu Van; Tien, Vu Dinh; Thuy, Vu Thu; Thi Thao, Do; Nam, Nguyen Hai; Koeckritz, Angela; Vu, Tran Khac; Journal of Chemistry; vol. 2017; (2017);,
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5788-17-0, A common heterocyclic compound, 5788-17-0, name is Methyl trans-3-methoxyacrylate, molecular formula is C5H8O3, 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.

4-Amino-5-[1-methoxy-2-(methoxycarbonyl)ethenyl]-7-(2-C- methyl-ss-D-ribofurnaosyl)-7H-pyrrolo [2,3-d]pyrimidine (13.1) [0191] To a solution of compound 11.2 (200 mg, 0.492 mmol) in 5 mL of anhydrous DMF were added Cul (19 mg, 0.2 eq. ), E-3-methoxymethacrylate (1. 06 mL, 20 eq.), triethylamine (137 7 LL, 2 eq. ) and Pd (PPh3) 4 (57 mg, 0.1 eq. ) at room temperature under an argon atmosphere. The reaction mixture was heated at 70C for 24 hr. then cooled to room temperature and 100 mL of 1/1 MeOH/CH2Cl2 was added. 400 mg Dowex 1×2-100 Bicarb form was then added and the suspension stirred at room temperature for 45 min. , then filtered. The resin was washed with 3X10 ML MEOH/CH2CL2 : 111. DMF was finally evaporated by azeotropic co-evaporation with toluene (2×5 mL). Chromatographic purification of the residue on silica gel (eluent: CH2CL2/MEOH : 95/5) gave 87 mg of product 13.1 (yield: 45%).

The synthetic route of 5788-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTA, INC.; WO2005/21568; (2005); A2;,
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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. 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, This compound has unique chemical properties. The synthetic route is as follows., 5616-81-9

Synthesis of (25,4a5,6a5,6bR, 8aR, 1OS,1 2a5, 1 2bR, 1 4bR)-Benzhydryl 1 O-(3 -((2-tert-butoxy-2- oxoethyl)(methyl)amino)-2-hydroxypropoxy)-2,4a,6a,6b,9,9, 1 2a-heptamethyl- 13 -oxo- 1,2,3 ,4,4a, 5,6,6a,6b,7,8,8a,9,1O,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (95-1). A solution of 82-2 (40 mg, 0.058 mmol) and tert-butyl sarcosine (46 mg, 0.32 mmol) in THF (0.50 mL) and water (0.10 mL) was heated at 65C for 5 hours. The reaction was concentrated to drynessand purified by flash chromatography (4g 5i02, 0-5% MeOHIDCM) to give the title compound (47 mg).

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; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
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Adding some certain compound to certain chemical reactions, such as: 3196-15-4, name is Methyl 2-bromobutyrate, 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 3196-15-4. 3196-15-4

[1014] Step 3: methyl 3-(1-methoxy-1-oxobutan-2-yl)-2-(4-methylbenzoylimino)-2,3-dihydrobenzo[d]thiazol-6-carboxylate[1015] To the mixture of methyl 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylate and 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylic acid (100 mg, 0.32 mmol) prepared in Step 2 in dimethylformamide (1.5 mL) were added potassium carbonate (133 mg, 0.96 mmol) and methyl 2-bromobutyrate (55 uL, 0.48 mmol). The reaction mixture was refluxed under stirring at 80 ? overnight. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with preparative thin layer chromatography (n-hexane/ethyl acetate = 4/1) to give 50 mg of the titled compound as a white solid (Yield: 37%).[1016] 1H NMR (DMSO-d 6 , 400 MHz) delta 8.61(s, 1H), 8.12(d, 1H), 8.06(d, 2H), 7.93(d, 1H), 7.34(d, 2H), 5.90(m, 1H), 3.90(s, 3H), 3.59(s, 3H), 2.40-2.50(m, 5H), 0.77(t, 3H)

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 Methyl 2-bromobutyrate.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
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