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Reference of 23877-12-5,Some common heterocyclic compound, 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, molecular formula is C8H15BrO2, 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.

Scheme 1. A solution of ethyl-(6-triisopropylsilanylsulfanyl-1, 2,3, 4- tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester (260.0 mg; 0.46 MMOL) and tert-butyl 11-BROMOISOBUTYL RATE (130 uL, 0.69 MMOL) in anhydrous THF (2 mL) was cooled to 0 C, a 1.0 M solution of TBAF (690 uL, 0.69 MMOL) was added, then the reaction was warmed to RT, stirred for 1 h, and then diluted with water, extracted with Et20 (3 times). The combined organic extracts were dried over NA2SO4, and the solvent removed under reduced pressure. The crude residue was purified by flash chromatography eluting with Hexane-EtOAc (7: 1) to provide 229.2 mg (90%) of 2- {6- [ETHYL- (4-TRIFLUOROMETHOXY- PHENOXYCARBONYL)-AMINO]-5, 6,7, 8-TETRAHYDRONAPHTHALEN-2-YLSULFANYL}-2-METHYL- propionic acid tert-butyl ester as a light-color oil. 1H NMR (300 MHz, CDCI3) : S 6.95-7. 28 (m, 7 H), 4.34 (m, 1H), 3.41 (m, 2H), 2.96 (m, 2H), 2.91 (m, 2H), 3.41 (m, 2H), 2.06 (m, 2H), 1.44 (s, 6H), 1.42 (s, 9H), 1.28 (m, 3H) LC/MS: C28H34F3NO5SNA : m/z 576 (M+NA)

The synthetic route of 23877-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/37779; (2004); A1;; ; Patent; JANSSEN PHARMACEUTICA, N.V.; Demarest, Keith, T.; WO2004/37778; (2004); A1;,
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Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

Step 2 Ethyl 4-oxocyclohexanecarboxylate (33.0) STR44 To a 3-L 3-neck flask equipped with a mechanical stirrer, a thermometer, and an addition funnel were added 50 g (292 mmol) of the compound of Formula 32.0 from Step 1, 33 mL (584 mmol) of acetic acid and 145 mL of commercial bleach (5.25percent NaOCl). To the cooled reaction mixture, at 5¡ã C., was added dropwise 479 mL of more bleach. The reaction was allowed to warm to room temperature for 1 hour and then was extracted with 3*400 mL ethyl acetate. The combined extract was washed with water, dried over MgSO4, and concentrated to give 49 g of crude 33.0 as an oil which was used without purification. The spectrum data are identical to that of literature (see Sanchez, I. H.; Ortega, A.; Garcia, G.; Larraza, M. I.; Flores, H. J. Synthetic comm. 1985, 15, 141).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US5648484; (1997); A;,
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Related Products of 15568-85-1, 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 15568-85-1 as follows.

General procedure: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.5 g, 2.9 mmol) was added to a stirred solution of the 5-aminopyrazole 6 (2.9 mmol) in MeCN (10 mL). After stirring for 1 h, the solvent was removed in vacuo to complete the precipitation of the product.

According to the analysis of related databases, 15568-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mackay, Martha; Nortcliffe, Andrew; McNab, Hamish; Hulme, Alison N.; Synthesis; vol. 47; 2; (2015); p. 242 – 248;,
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Reference of 6065-82-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6065-82-3 name is Ethyl diethoxyacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

TMSOTf (0.33 mL, 1.85 mmol) was added to a suspended solution of 25 (209.0 mg, 0.443 mmol) and ethyl diethoxyacetate (83.0 mL, 0.46 mmol) in dichloroethane (15 mL), and the reaction mixture was heated at 120 C for 13 h. The reaction mixture was diluted with saturated NaHCO3 (200 mL) and extracted with chloroform (3¡Á200 mL). The combined extracts were washed with brine (200 mL), dried, and concentrated in vacuo to give a residue (246 mg). Chromatography of this residue on a silica gel (120 g) column with dichloromethane-methanol (50/1) gave 26 (190.0 mg, 77.1%) as a pale yellow amorphous powder, the recrystallization of which from ethyl acetate-ether afforded 26 as colorless prisms, mp 253-254 C. IR (KBr) 3399, 2940, 1732, 1639, 1460, 1422, 1350, 1281, 1192, 1117, 1067 cm-1; 1H NMR (CDCl3, 500 MHz) delta 1.28 (3H, t, J=7.0 Hz, OCH2CH3), 2.06 (3H, s, 12-CH3), 2.11 (3H, s, 3-CH3), 2.30 (1H, dd, J=16.8, 10.4 Hz, 14-Hbeta), 2.54 (3H, s, NCH3), 2.77 (1H, d, J=17.7 Hz, 5-Hbeta), 2.94 (1H, dd, J=16.8, 5.5 Hz, 14-Halpha), 2.95 (1H, dd, J=17.7, 8.1 Hz, 5-Halpha), 3.72 (3H, s, 2-OCH3), 3.77 (3H, s, 10-OCH3), 3.79 (3H, s, 11-OCH3), 3.82 (1H, d, J=8.1 Hz, 6-H), 3.86 (3H, s, 1-OCH3), 4.18 (1H, dq, J=10.7, 7.0 Hz, OCHCH3), 4.25 (1H, dq, J=10.7, 7.0 Hz, OCHCH3), 4.36 (1H, dd, J=5.5, 1.5 Hz, 15-H), 4.51 (1H, dt, J=10.4, 5.5 Hz, 14a-H), 4.80 (1H, br s, OH), 6.46 (1H, s, 9-H); 13C NMR (CDCl3, 125 Hz) delta 8.7 (3 or 12-CH3), 8.8 (3 or 12-CH3), 14.2 (OCH2CH3), 23.5 (C5), 24.8 (C14), 40.3 (NCH3), 50.6 (C9), 52.3 (C14a), 54.6 (C15), 58.5 (C6), 60.1 (2-OCH3), 60.2 (10 or 11-OCH3), 60.3 (10 or 11-OCH3), 60.7 (1-OCH3), 61.7 (OCH2CH3), 114.7 (C4a), 115.3 (C9a), 117.5 (C3 or C12), 117.7 (C3 or C12), 121.8 (C13a), 122.9 (C15a), 143.8 (C10), 144.4 (C1), 146.9 (C13), 148.3 (C4), 149.3 (C2), 149.6 (C11), 169.9 (C7), 171.3 (C16); EIMS m/z 556 (M+, 20), 484 (10), 234 (100); HREIMS m/z 556.2421 (M+, calcd for C29H36N2O9, 556.2421). Anal. Calcd for C29H36N2O9: C, 62.58; H, 6.52; N, 5.03. Found: C, 62.79; H, 6.68; N, 4.98.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl diethoxyacetate, and friends who are interested can also refer to it.

Reference:
Article; Yokoya, Masashi; Shinada-Fujino, Kimiko; Yoshida, Saiko; Mimura, Masahiro; Takada, Hiroki; Saito, Naoki; Tetrahedron; vol. 68; 22; (2012); p. 4166 – 4181;,
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Application of 849758-12-9, 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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 4-bromo-3-fluoro-benzoic acid methyl ester (1 g, 4.29 mmol), hydrazine hydrate (2.2 ml_, 42.9 mmol) and MeOH (20 ml_) was heated at 70 C for overnight. Concentrated, diluted with EtOAc (300 ml_) and washed with water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated give the desired product 2AR (0.9 g, 90%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-3-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
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Synthetic Route of 207346-42-7, These common heterocyclic compound, 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, 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 2; Synthesis of f4-(6-fluoro-7-methylamino-2,4-dioxo-l,4-dihydro-2H- quinazolin-3-yI)-phenyll-5-chloro-thiophen-2-yl-sulfonyIurea (7a)Step i.Ia 2a 2b[0276] Aniline 1 (1H NMR (DMSO): delta 7.58 (dd, IH), 6.72 (dd, IH), 3.77 (s, 3H); 6.0 g, 32.085 mmol) was placed in a 500 mL round bottomed flask and 20% phosgene in toluene (175 mL, 332.50 mmol, 10.36 equiv) was added. The resulting somewhat sticky suspension was then magnetically stirred overnight at room temperature resulting in a clear, colorless solution. An aliquot removed, blown dry with argon, quenched with MeOH, and analyzed by RP-HPLC/MS to show no unreacted aniline 1 and clean formation of the isocyanate 2a and/or carbamoyl chloride 2b as analyzed as its methyl-carbamate. The mixture was concentrated first by rotary evaporation and then under high vacuum to yield 6.76g (99% yield) of the isocyanate 2a and/or carbamoyl chloride 2b as a free-flowing white solid.

Statistics shows that Methyl 2-amino-4,5-difluorobenzoate is playing an increasingly important role. we look forward to future research findings about 207346-42-7.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2008/137809; (2008); A2;,
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Synthetic Route of 142166-01-6, 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. 142166-01-6, name is Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

3, 4-Dihydro-2H-benzo [1, 4] oxazine-7-carboxylic acid methyl ester (52 mmol) was dissolved in MeOH (20 mL) and NaOH (2M) (20 mL) and stirred at 60 C for 48h. The organic solvent was removed by evaporation, and the aqueous phase acidified with HC1 (4M). The organic products separated as an oil, and were extracted with ethyl acetate. The organic extract was dried over MgS04, filtered and evaporated. The crude was purified by flash chromatography on silica with gradient elution (heptane/ethyl acetate). Yield: 31 % 1H NMR (D6-DMSO) : 3.33 (t, 2H); 4.10 (t, 2H); 6.51 (d, 1H); 7.16 (d, 1H); 7.30 (dd, 1H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; WO2005/39572; (2005); 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. 4519-46-4, name is Methyl 2-bromoacrylate, A new synthetic method of this compound is introduced below., Formula: C4H5BrO2

EXAMPLE 5 2-Benzyloxycarbonyl-7-bromo-7-methoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene To 40 g. (0.2 moles) of N-benzyloxycarbonyl-1,2-dihydropyridine prepared as described in Example 3, 38 g. (0.23 moles) of freshly prepared methyl alpha-bromoacrylate and 2 g. of hydroquinone are added. The reaction mixture is allowed to stand at room temperature for 48 hours, under protection from light. The completion of the cycloaddition is shown by the disappearance of the lambdamax =305 nm from the UV spectrum. The reaction mixture is evaporated to an oily residue in vacuo, on a water bath of 40-50 C., and extracted from three 40-ml. portions of a benzene/brine mixture. The benzene phase is dried over magnesium sulfate and evaporated in vacuo, whereupon it is column chromatographed on a 30-fold amount of Kieselgel (0.063-0.2 mm), using a 10:1 mixture of benzene and ethyl acetate for the elution. Yield: 8 g. (0.01 moles), 11% based on the starting pyridine

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; Richter Gedeon Vegyeszeti Gyar Rt.; US4563464; (1986); 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 40258-78-4 as follows. Safety of 1-Bromoethyl acetate

[5-(6-Chloro-5-cyano-1-methansulfonyl-1H-indol-2-yl)-6-(2-methoxyethoxymethoxy)biphenyl-3-yloxylacetic acid ethyl ester 260A mixture of 6-chloro-2-[5-hydroxy-2-(2-methoxyethoxymethoxy)biphenyl-3-yl]-1-methansulfonyl-1H-indole-5-carbonitrile (7.0 g, 13 mmoles) and K2CO3 (5.5 g, 23 mmoles) in acetonitrile (200 ml), was mixed with NaI (0.5 g) and bromoethyl acetate (1.6 ml, 14 mmoles). The mixture was stirred for about 18 h at ambient temperature, concentrated, the residue was dissolved in ethyl acetate (400 ml) and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated to afford 8.0 g (98percent) of the title compound as a brown foam.

According to the analysis of related databases, 40258-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Axys Pharmaceuticals, Inc.; US6867200; (2005); B1;,
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Related Products of 52449-43-1, 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 52449-43-1 as follows.

Example 50AMethyl (4-chlorophenyl)(cyclopentyl)acetate; A suspension of 3.65 g (32.5 mmol) of potassium tert-butoxide in 65 ml of abs. DMF was cooled to 0 C., and a solution of 5.0 g (27.08 mmol) of methyl 4-chlorophenylacetate in about 2 ml of abs. DMF was added dropwise. The mixture was stirred at 0 C. for 30 min, and 4.84 g (32.5 mmol) of cyclopentyl bromide were then slowly added dropwise. The reaction mixture was stirred at 0 C. for 1 h and then added to water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1). This gave 6.28 g of the target compound (91.8% of theory).GC-MS (Method 1): Rt=6.07 min; m/z=193 (M-C2H3O2)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.96-1.04 (m, 1H), 1.08-1.37 (m, 2H), 1.37-1.48 (m, 1H), 1.49-1.70 (m, 3H), 1.79 (dtd, 1H), 2.33-2.50 (m, 1H), 3.42 (d, 1H), 3.58 (s, 3H), 7.29-7.46 (m, 4H).

According to the analysis of related databases, 52449-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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