Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 57486-68-7, name is Methyl 2-chlorophenylacetate, 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 57486-68-7, COA of Formula: C9H9ClO2

66.5 g (0.36 mol) of methyl o-chlorophenylacetate (III), 80 mL of tetrahydrofuran, and 8.9 g (0.37 mol) of sodium hydride were weighed.After stirring and dissolving, sodium hydride was completely dissolved, and then methyl 1-chlorocyclopropane-1-carboxylate 50 g (0.36 mol) was slowly added.Warm up to reflux, keep warm for 4h, gas phase tracking 1-chloro-1-carboxylic acid methyl ester-cyclopropane conversion rate of 99% or more, cooling to 20 ~ 25 C,The reaction solution was quenched by adding 60 mL of a 10% dilute hydrochloric acid solution, and 3.2 g (0.1 mol) of tetrabutyl bromide was added.The temperature is refluxed, the temperature is kept for 5 hours, the temperature is lowered to 20 to 25 C, and the organic phase is separated.The aqueous phase (50 mL x 2), extract the aqueous phase, and combine the organic phases.Desolventizing have to compound IV, as a pale yellow liquid 68g, 96% yield.

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; Anhui Jiuyi Agricultural Co., Ltd.; Shen Yunhe; Xiong Guoyin; Yu Zhenglian; Zhao Xiaojun; Zhou Quanquan; Fan Fuyun; (12 pag.)CN109369549; (2019); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17205-02-6 as follows. HPLC of Formula: C7H12O3

3-hydroxy-cyclobutane-carboxylic acid ethyl (800 mg)In tetrahydrofuran (25mL) solution,Reference Example 2-53 (1) synthesized in 2-chloro-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.24 g),Triphenylphosphine (5.68g),Toluene solution of diethyl azodicarboxylate (2.2M, 9.84mL) was added,It was stirred at room temperature for 13 hours. The temperature was raised to 60 , and the mixture was stirred for 7 hours at the same temperature.The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) in the purified twice, to give the title compound (3.63g) as a colorless solid .

According to the analysis of related databases, 17205-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
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Electric Literature of 680-65-9, 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. 680-65-9, name is Diethyl difluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 152. Preparation of 4-((lR,3aS,5aR,5bR,7aR,llaS,llbR,13aR,13bR)-3a ((3-(2-(dimethylamino)ethylamino)-2,2-difluoro-3-oxopropanamido)methyl)- 5a,5b,8,8, 11 a-pentamethyl- 1 -(prop- 1 -en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1: Preparation of the C28 reversed amide To a solution of tert-butyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- (aminomethyl)-5a,5b,8,8, 11 a-pentamethyl-1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (200 mg, 0.333 mmol) in methanol (5 ml) and 1,4-dioxane (5 ml) was added diethyl 2,2-difluoromalonate (654 mg, 3.33 mmol). The resulting solution was stirred at rt for 6 days. The reaction mixture was concentrated in vacuo. The crude product was purified by Biotage (Thomson 25 g silica gel column; 4: 1 Hex/EtOAc) to give 116 mg (47 %) of product. MS: m/e 736.6 (MH+), 2.86 min (method 2). ? NMR (400 MHz, CHLOROFORM-d) delta ppm 0.93 (s, 6 H) 0.99 (s, 3 H) 1.02 (s, 3 H) 1.13 (s, 3 H) 1.60 (s, 9 H) 1.71 (s, 3 H) 0.85 – 1.83 (20 H) 1.98 – 2.10 (m, 1 H) 2.10 (dd, J=17.07, 6.27 Hz, 1 H) 2.49 (td, J=l 1.04, 5.27 Hz, 1 H) 3.16 (dd, J=13.55, 6.27 Hz, 1 H) 3.65 (dd, J=14.43, 7.15 Hz, 1 H) 3.95 (s, 3 H) 4.61 – 4.65 (m, 1 H) 4.73 (d, J=1.76 Hz, 1 H) 5.28 (dd, J=6.15, 1.63 Hz, 1 H) 6.28 (t, J=7.03 Hz, 1 H) 7.18 (d, J=8.53 Hz, 2 H) 7.89 (d, J=8.28 Hz, 2 H). iyF NMR (376 MHz, CHLOROFORM-d) delta ppm -112.49 (s, 2 F).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; SWIDORSKI, Jacob; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; LIU, Zheng; WO2012/106188; (2012); A1;,
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Related Products of 754125-43-4, The chemical industry reduces the impact on the environment during synthesis 754125-43-4, name is Methyl 3-(cyclopentylamino)propanoate, I believe this compound will play a more active role in future production and life.

To a stirred solution of methyl 3-(cyclopentylamino)propanoate (6.0 g, 35.0 mmol) and potassium carbonate (7.3 g, 52.6 mmol) in 150 mL of acetone was slowly added 2,4-dichloro-5-nitropyrimidine (6.8 g, 35.0 mmol, dissolved in 50 mL acetone) at 0 “C. The reaction mixture was stirred and allowed to approach room temperature over a period of 12-16 hours. After the reaction was complete as monitored by reverse phase analytical liquid-chromatography electrospray mass spectrometry (LC-MS), the solvent was removed in vacuo. The resulting slurry was then diluted in water and brine and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica- gel chromatography with dichloromethane:methanol (100:1 v/v) to give the title compound I-l-a (8.0 g, 69percent), MS (ESI) m/z 329 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3-(cyclopentylamino)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DANA FARBER CANCER INSTITUTE; GRAY, Nathanael, S.; DENG, Xianming; KWIATKOWSKI, Nicholas, Paul; WO2010/80712; (2010); A2;,
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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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Recommanded Product: 35179-98-7

To a solution of ((R)-3~benzyloxycarbonylamino-2-hydroxy- EPO propyO-cyclohexylmethyl-phosphinic acid (1.0 g, 2.71 mmol) and carbonic acid chloromethyl ester ethyl ester (1.13 g, 8.16 mmol) in toluene (60 mL) was added silver carbonate (2.26 g, 8.16 mmol). The reaction mixture was heated at reflux for 3h. The reaction mixture was then filtered and was concentrated in vacuo. Purification by gradient flash chromatography (methanol/methylene chloride) on a 35 g RediSep disposable column gave (3- benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid ethoxycarbonyloxymethyl ester (300 mg, 0.63 mmol). 1H-NMR(CDCl3, 300 MHz): delta 7.35 (m, 5H), 5.65 (m,2H), 5.45 (br s, IH), 5.10 (s, 2H), 4.2 (m, 2H), 3.45 (dd, IH), 3.20 (dd, IH), 2.01-1.55 (m, HH), 1.40-0.95 (m, 8H).

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/86734; (2006); A1;,
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Synthetic Route of 816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 cis-l-amino-4-((tert-butyldimethylsilyl)oxy)-5-phenylpyrrolidin-2-one (9.0 g, 29.4 mmol) and ethyl 2-ethoxy-2-imino-acetate (21.3 g, 146.8 mmol) in toluene (500 mL) was heated at 90 C for 18 h and concentrated under reduced pressure. The residue was diluted with water (200 mL) and extracted with ethyl acetate (3 x 150 mL). The combined organic layers were concentrated under reduce pressure to afford crude ethyl cis-2-((3-((tert-butyldimethylsilyl)oxy) -5-oxo-2- phenylpyrrolidin-l-yl)amino)-2-iminoacetate (10.0 g, 84%) as a brown oil. LC-MS RT= 1.128 min, m/z = 406.4 [M + H]+. LCMS (10 to 80% acetonitrile in water + 0.03% trifluoacetic acid over 2.0 in, ESI+ found [M+H] = 406.4.

Statistics shows that Ethyl 2-ethoxy-2-iminoacetate is playing an increasingly important role. we look forward to future research findings about 816-27-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
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Related Products of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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.

[0714] To a solution of 6.0 g (24 mmol) OF 2-HYDROXY-5-IODOBENZALDEHYDE and 5 mL (33.3 mmol) of ethyl 4,4, 4-trifluorocronate in 20 mL of dry DMF at 60 C was added potassium carbonate in one portion. The mixture was stirred at 60 C overnight. After cooling to room temperature, the solid was filtered and washed with EtOAc. The combined filtrates were diluted by addition with 300 mL EtOAc and washed with brine. The organic phase was dried over anhydrous magnesium sulfate and evaporated to afford an oil, which was further purified silica gel chromatography with EtOAc/hexane (1: 9). Concentration of the desired fractions afforded 4.7 g (49%) of a light yellow solid : H NMR (CDCL3/300 MHz) 7.65-7. 55 (m, 3H), 6.78 (d, J=8. 4Hz, 1H), 5.72 (q, J=6. 6 Hz, 1H), 4.34 (m, 2H), 1.37 (t, J=6. 9 Hz, 3H). MS (ES+) 398.9 (M+H, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4,4,4-trifluorocrotonate, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Synthetic Route of 61644-18-6, A common heterocyclic compound, 61644-18-6, name is Chloromethyl isobutyrate, molecular formula is C5H9ClO2, 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.

Example 9 Preparation of (Z)-(N’-(2,6-dimethylphenyl)-N-(2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropyl)-carbamimidoylthio)methyl isobutyrate (Compound 15) To a solution of 1-(2,6-dimethylphenyl)-3-(2-(4-(1-(4-(trifluoromethoxy)-phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropyl)thiourea (75 mg, 0.143 mmol) in chloroform (CHCl3; 0.72 mL) was added chloromethyl isobutyrate (31.1 mg, 0.172 mmol). The mixture was heated at 100 C. for 1 h. The mixture was cooled to 25 C., and the residue was purified by silica gel chromatography (EtOAc-hexanes gradient) to afford the title compound (17.3 mg, 19%) as a yellow oil: IR vmax 3332 (br), 3124, 2976, 2939, 1739, 1631, 1590, 1518, 1264, 1171, 986 cm-1; 1H NMR (400 MHz, CDCl3) delta 8.54 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.37 (d, J=8.3 Hz, 2H), 7.20 (d, J=7.2 Hz, 2H), 7.02 (d, J=7.5 Hz, 2H), 6.88 (t, J=7.5 Hz, 1H), 5.65 (br s, 2H), 2.88 (br s, 1H), 2.68-2.52 (m, 1H), 2.10 (s, 6H), 1.82-1.46 (m, 2H), 1.46-1.22 (m, 2H), 1.22-1.18 (m, 6H); ESIMS m/z 624 (M+H).

The synthetic route of 61644-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Crouse, Gary D.; Lambert, William T.; Sparks, Thomas C.; Hegde, Vidyadhar B.; US2012/202688; (2012); A1;,
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Reference of 1459-93-4,Some common heterocyclic compound, 1459-93-4, name is Dimethyl isophthalate, molecular formula is C10H10O4, 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.

3-Ethynylaniline (3) (0.6 mL, 5.6 mmol) was dissolved in THF (15 mL) in the presence of n-butyllithium (1.6 M in hexane, 3.5 mL, 5.6 mmol) and the mixture was stirred at -78 C for 30 min, then dimethyl isophthalate (4) (1 g, 5.15 mmol) was added dropwise to the mixture and the solution was stirred overnight under N2. After removing solvent by evaporation, the crude product was purified by recrystallization from methanol to obtain 5 (1.3 g, 4.65 mmol, 90%). 1H NMR (300 MHz, DMSO-d6) delta 8.60 (s, 1H), 8.21 (m, 2H), 7.90 (m, 1H), 7.74 (d, J = 8.13 Hz, 1H), 7.66 (t, J = 7.80, 7.80 Hz, 2H), 7.37 (t, J = 7.88, 7.88 Hz, 1H), 7.28 (d, J =7.69 Hz, 1H), 3.97 (s, 3H), and 3.52 (s, 1H) ppm. 13C NMR (75 MHz, DMSO-d6) delta 166.24, 165. 32, 135.76, 134.33, 133.85, 132.62, 131.03, 130.43, 128.75, 128.44, 126.21, 126.02, 122.11, 121.78, 84.12, 83.78, and 50.07 ppm. ESI-MS m/z: Observed 278.25 [M-H]-, [M-H]- calcd = 278.09.

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

Reference:
Article; Choi, Yeonweon; Jung, Sung Ho; Lee, Areum; Seo, Moo Lyong; Jung, Jong Hwa; Bulletin of the Korean Chemical Society; vol. 36; 6; (2015); p. 1725 – 1728;,
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