Category: esters-buliding-blocks

These common heterocyclic compound, 213598-10-8, name is Methyl 3-bromo-4-isopropoxybenzoate, 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. SDS of cas: 213598-10-8

Description 4: Methyl 3-cyano-4[(1-methylethyl)oxy]benzoate To a solution of methyl 3-bromo-4-[(1-methylethyl)oxy]benzoate (25 g, 91.575 mmol) (Description 3) in DMF (250 mL), under a nitrogen atmosphere, was added zinc cyanide (43 g, 366.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (21 g, 18.32 mmol) and the reaction mixture heated to 120 C. and stirred overnight. After cooling, the mixture was filtered and the filtrate combined with an identical reaction performed on the same scale and DCM (1.5 L) and water (1.5 L) added. The organic phase was separated and the aqueous phase was extracted with DCM (3×300 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica (petroleum ether :ethyl acetate (20:1) to afford the title compound (36 g). 1H NMR (CDCl3, 400 MHz) 5 ppm: 1.45 (6H, d, J=6.0 Hz), 3.92 (3H, s), 4.76 (1H, m), 7.00 (1H, d, J 9.0), 8.19 (1H, dd, J 9.0, 2.0 Hz), 8.26 (1H, d, J=2.0 Hz).

The synthetic route of Methyl 3-bromo-4-isopropoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO WELLCOME HOUSE; US2012/283297; (2012); A1;,
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Reference of 681128-38-1,Some common heterocyclic compound, 681128-38-1, name is Ethyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C7H10F2O2, 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 the compound described in Preparation 42 (2.30 g, 14 mmol), in diethyl ether (14 ml_), was added to a suspension of lithium aluminium hydride (1.17 g, 30.8 mmol), in diethyl ether (70 ml_), cooled to -45 0C. This mixture was stirred at -45 0C for 1 hour, then warmed to -10 0C for 1 hour. It was then slowly warmed to room temperature and stirred for 15 hours, After which time it was cooled to 4 0C and quenched with sequential addition of water (1.2 ml_), 10% aqueous solution of sodium hydroxide (1.2 ml_) and finally water (3.6 ml_). Diethyl ether (50 ml_) was then added and the solution was allowed to stir for 90 minutes. The organic layer was separated and the aqueous phase was back extracted with diethyl ether (3 x 50 ml_). The combined organic layers were dried over magnesium sulphate, filtered, and concentrated under reduced pressure to give a 45% solution of the title compound in diethyl ether (1.56 g, 92%). 1H-NMR (400 MHz, CDCI3): delta 2.30 (m, 3H), 2.60 (m, 2H), 3.65 (m, 2H).

The synthetic route of 681128-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; GIBSON, Karl Richard; GREEN, Martin Peter; UNDERWOOD, Toby James; WAKENHUT, Florian; WO2010/32200; (2010); A1;,
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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 816-27-3 as follows. SDS of cas: 816-27-3

To a solution of 1-amino-5-(1,1-difluoropropyl)pyrrolidin-2-one (120 mg, 0.67 mmol) in ethanol (5 mL) was added ethyl 2-ethoxy-2-imino-acetate (489 mg, 3.37 mmol). The reaction mixture was stirred at 60 C. for 16 h and subsequently concentrated under reduced pressure to afford ethyl 2-[[2-(1,1-difluoropropyl)-5-oxo-pyrrolidin-1-yl]amino]-2-imino-acetate (600 mg, 80%, 40% purity) as a yellow oil, used as is in the next step.

According to the analysis of related databases, 816-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89901-03-1, name is Methyl 4′-bromo-[1,1′-biphenyl]-4-carboxylate, 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 89901-03-1, SDS of cas: 89901-03-1

To a round bottom flask was added methyl 4′-bromobiphenyl-4- carboxylate (2.0 g, 6.87 mmol, 1 .0 equiv) followed by a solution of racemic 2-trans- ethynylcyclopropyl)methanol (0.991 g, 10.30 mmol, 1.5 equiv) dissolved in THF (20 ml_). To this was added palladium dichloride bis-triphenylphosphine (241 mg, 0.343 mmol, 0.05 equiv), copper(l) iodide (131 mg, 0.687 mmol, 0.1 equiv), then triethylamine (6.87 ml_, 49.3 mmol, 7.18 equiv). The reaction was stirred at 75C for ~2 h. The reaction was cooled to room temperature, the solids filtered off, rinsing with THF. The solution was placed in the freezer for 5 days. Concentrate down to dryness. Add DCM and a precipitate forms. Filter precipitate, rinse with minimal DCM. TLC shows ppt contains mostly product (~1.5g solid). Triturate with 10%EtOAc in hexanes (5 mL), pipet off solvent, TLC shows solid contains product and liquid removed starting material-bromide and some baseline impurities. Additional 10%EtOAc in hexanes (5 mL) was added and stirred for 30 minutes, filtered, rinsed with 10%EtOAc in hexanes (5mL), and dried solid. Yielded 900 mg crude methyl 4′-(((1 ,2-irans)-2- (hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-carboxylate. 1 H NMR (DMSO-d6): delta 0.82-0.85 (m, 2H), 1.35-1.43 (m, 2H), 3.23-3.29 (m, 1 H), 3.40-3.42 (m, 1 H), 3.84 (s, 3H), 4.65-4.67 (t, 1 H), 7.43-7.45 (d, 2H), 7.67-7.70 (d, 2H), 7.80-7.82 (d, 2H), 7.99- 8.01 (d, 2H)

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 4′-bromo-[1,1′-biphenyl]-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHAOGEN, INC.; KASAR, Ramesh; LINSELL, Martin Sheringham; AGGEN, James Bradley; LU, Qing (Jane); WANG, Dan; CHURCH, Tim; MOSER, Heinz E.; PATTEN, Phillip A.; WO2012/154204; (2012); A1;,
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Some common heterocyclic compound, 1214334-90-3, name is Methyl 2-bromo-4-(trifluoromethyl)benzoate, molecular formula is C9H6BrF3O2, 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: 1214334-90-3

A 20 mL muwave vial was charged with methyl 2-bromo-4-(trifluoromethyl)benzoate (306 mg, 1.08 mmol), propane-2-sulfonamide (266 mg, 2.16 mmol), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (112 mg, 0.108 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (188 mg, 0.324 mmol), potassium phosphate tribasic (1.15 g, 5.41 mmol) and toluene (10.0 mL). The vial was sealed, purged with nitrogen for 5 min, and then heated at 100 C. for 18 hours. The reaction was cooled to room temperature, concentrated and diluted with water. The mixture was extracted with EtOAc (3×), washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography to afford methyl 2-((1-methylethyl)sulfonamido)-4-(trifluoromethyl)benzoate. LCMS-ESI+ (m/z): [M+H]+ calcd 326.07; found 326.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1214334-90-3, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Farand, Julie; Kaplan, Joshua A.; Notte, Gregory; Olen, Casey Lockwood; Sangi, Michael; Sperandio, David; (115 pag.)US2019/359565; (2019); 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. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H12O4

Methyl 4-(2-methoxy-2-oxoethyl)benzoate (100 mg, 0.48 mmol), methanol (1.5 mL), water (1.5 mL) and anhydrous potassium carbonate (116 mg, 0.72 mmol) were added in a 10 mL single-neck flask, and the mixture was stirred at room temperature for 1.5 hours. After the materials had all reacted when being determined by TLC, solvent was removed in vacuo, and the residue was redissolved in ethyl acetate (1 mL) and separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give a product (white solid, 60 mg), with a yield of 64.4%. 1H NMR (400 MHz, CDCl3) delta 8.00 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 3.91 (s, 3H), 3.70 (s, 2H).

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; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
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Electric Literature of 109232-37-3,Some common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, molecular formula is C11H21ClO2, 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 solution of phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or 5-chloro-2,2-dimethylpentanoic acid isobutyl ester) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N’-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15.

The synthetic route of 109232-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Filippis, Barbara; Giancristofaro, Antonella; Ammazzalorso, Alessandra; D’Angelo, Alessandra; Fantacuzzi, Marialuigia; Giampietro, Letizia; MacCallini, Cristina; Petruzzelli, Michele; Amoroso, Rosa; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 5218 – 5224;,
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Electric Literature of 106-65-0, A common heterocyclic compound, 106-65-0, name is Dimethyl succinate, molecular formula is C6H10O4, 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 11 Methyl alpha-formylsuccinate In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.50 mol) and methylformate (123 mL, 2.00 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and dimethyl succinate in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of dimethyl succinate by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet,ibid, had reported a 62% yield. 1H-NMR (DMSO-d6/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d6/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).

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; Nielsen, Peter E.; US6300318; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, 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. Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

[01355] Step 4: Synthesis of cis and trans methyl 5-bromo-3-((4-((tert-butoxycarbonyl)amino) cyclohexyl) amino -2-methylbenzoate[01356] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (5.6 g, 26.7 mmol) in methanol (50 mL), acetic acid ( 1 .2 g, 20.57 mmol) was added and reaction stirred at room temperature for 8 h. Then sodium cyanoborohydride (1.6 g, 26.74 mmol) was added at OoC and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography twice eluting with ethyl acetate: hexane to afford (4g , 44%) of less polar cis isomer and (3g, 33%) of the pure more polar trans isomer.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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Related Products of 7364-20-7, These common heterocyclic compound, 7364-20-7, name is Methyl 4-ethylbenzoate, 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: (Diacetoxyiodo)benzene (5 mmol, 1.61 g), I2 (0.4 mmol, 102 mg), p-toluenesulfonamide (0.4 mmol, 68.4 mg), and ethylbenzene (2 mmol, 184 mg) were added to dichloroethane (3 mL). The mixture was warmed at 60 C for 2 h under an argon atmosphere. Then, the mixture was poured into saturated aqueous sodium sulfite solution and extracted with diethyl ether (3 × 20 mL). The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was subjected to preparative TLC on silica gel using a mixture of hexane and ethyl acetate (5:1) as an eluent to give alpha-(acetoxy)ethylbenzene in 63% yield.

Statistics shows that Methyl 4-ethylbenzoate is playing an increasingly important role. we look forward to future research findings about 7364-20-7.

Reference:
Article; Baba, Haruka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 52; 33; (2011); p. 4303 – 4307;,
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