Esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, 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 84228-44-4, Recommanded Product: 84228-44-4

To a solution of methyl 4-amino-3-chlorobenzoate (0.37g, 0.002 mol) and diisopropylethylamine (0.39g, 0.003 mole) in dioxane at ambient temperature was added in one portion 2-oxo-l ,2-dihydro-3-pyridinecarbonyl chloride (0.4g, 0.002 mol) [prepared as described in WO/201 1/088201 Al]. The mixture was heated at reflux for 24 h. after which it was cooled to ambient temperature and partitioned between EtOAc and water. The two phase material was filtered and the solid was washed with water, then EtOAc and air dried to obtain a 25% yield of the title compound as an off-white solid. MS: m z 305 (MIT) and m/z 307 (MH+). NMR (500 MHz, DMSO-d6): delta 3.848 (s, 3H), 6.604 (t, 1H), 7.878 (qd, 1H), 7.942 (dd, 1H), 8.015 (d, 1H), 8.504 (dd, 1H), 8.744 (d, 1H), 12.787 (br s, 1H), 12.893 (s, 1H).

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-amino-3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NORTH CAROLINA CENTRAL UNIVERSITY; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; SEXTON, Jonathan Z.; BRENMAN, Jay E.; WO2014/165816; (2014); A1;,
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Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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. Quality Control of Methyl 2-bromo-2-methylpropanoate

A 12 L, 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser and nitrogen bubbler, was charged with malononitrile (251 g, 3.802 moles) and THF (2 liters). Potassium t-butoxide (1M THF, 3.802L, 3.802 moles) was then added. The mixture was stirred at 50C for 30 min. Methyl 2-bromoisobutyrate (688 g, 3.80 moles) was added and the reaction mixture was stirred overnight at 50C. The reaction was partitioned between aqueous 1 N HCI and EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to give the title product. 1H NMR (400 MHz, CD3CN): delta 4.35 (1 H, s) 3.73 (3 H, s), 1.43 (6 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23426-63-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); A1;,
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Synthetic Route of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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 solution of (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H2O (2.06 g, 13.46 mmol), EDC.HCl (3.87 g, 20.20 mmol), methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500 ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100 g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1. Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg).(D73a) (syn diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1H), 7.90-7.76 (m, 2H), 7.34-7.19 (m, 2H), 4.52-4.35 (m, 1H), 3.84 (s, 3H), 3.43-3.32 (m, 1H), 2.67-2.39 (m, 1H), 1.88-1.74 (m, 1H), 1.52-1.33 (m, 10H), 1.27-1.12 (m, 4H), 1.09-0.92 (m, 1H), 0.66-0.53 (m, 1H).(D73b) (anti diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69-8.52 (s, 1H), 7.90-7.73 (m, 2H), 7.35-7.19 (m, 2H), 3.93-3.75 (m, 4H), 3.36-3.30 (m, 1H), 2.35-2.19 (m, 1H), 2.12-2.02 (m, 1H), 1.90-1.74 (m, 1H), 1.47-1.30 (m, 9H), 1.25-1.07 (m, 4H), 0.73 (td, J=5.4, 8.8 Hz, 1H), 0.39 (br. s., 1H).

The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
Ester – Wikipedia,
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Synthetic Route of 58656-98-7, 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 58656-98-7 as follows.

A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of 2-cyanoindole, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-2-cyanoindole as an oil.

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5380739; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 7149-03-3, A common heterocyclic compound, 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, molecular formula is C9H10BrNO2, 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.

Compound 11b (11.8 g, 48.34 mmol) was dissolved in concentrated hydrochloric acid (60.43 mL, 12N) at -10C, then a solution of sodium nitrite (4.00 g, 58.01 mmol) in water (300 mL) was added dropwise. The resulting reaction solution was reacted at 0C for 0.5 hour, and added at -10C in portions to another reaction vessel containing cuprous chloride (1.44 g, 14.50 mmol) and liquid sulfur dioxide (9.29 g, 145.03 mmol). . The resulting reaction solution was reacted at 0C for 0.5 hours. After extraction with ethyl acetate (100 mL¡Á3), the organic phase was washed with saturated brine (100 mL¡Á3), dried over anhydrous sodium sulfate, filtered, and concentrated to give compound 11c (14.00 g).

The synthetic route of 7149-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (2018); A;,
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Application of 2216-92-4, A common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, molecular formula is C10H13NO2, 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 Ethyl alpha-(N-pyrrolyl)-phenylacetate 52.8 g (0.24 mole) of ethyl phenylglycinate were dissolved in 136 ml of glacial acetic acid. Thereafter 39 g (0.24 mole) of 2,5-diethoxytetrahydrofuran were added over 10-15 minutes with stirring. The mixture was heated under reflux for one hour. After this time had elapsed, the mixture was allowed to cool and the major portion of the acetic acid was drawn off under reduced pressure. Finally, the residue was distilled under vacuum and the fraction distilling out at 115-118 C. at 0.2 mm Hg was collected. The product obtained was first a colourless oil which crystallized on cooling, adopting a waxy aspect and weighing 46.5 g (70%). M.p. 51-53 C. Centesimal composition: 73.31% C.; 6.08% N; 6.53% H. The IR spectrum in 0.5% KBr is illustrated in FIG. 1.

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; Antibioticos, S.A.; US4563477; (1986); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2065-23-8, name is Methyl 2-phenoxyacetate, 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 2065-23-8, HPLC of Formula: C9H10O3

General procedure: An aqueous CH3CN solution (CH3CN54 ml, H2O 6 ml) of N-Boc Val-OMe1a (0.6 mmol, 10 mM), phenanthrene(0.6 mmol, 10 mM), 1,4-dicyanobenzene (0.6 mmol, 10 mM) and NaOH (3 mmol, 50 mM)in three Pyrex vessels (18 mm x 180 mm) was purged with argon for 10 min andadded by acrylonitrile 2a (0.6 mmol,10 mM) under argon atmosphere. The mixture was heated by water bath at 40 for 2h and irradiated with a 100-W high-pressure mercury lamp for 3 h at roomtemperature. Then the mixture was evaporated, and the resulting residue wasdissolved in EtOAc and washed with water, dried over Na2SO4,and concentrated under reduced pressure. The product was purified by silica gelcolumn chromatography using hexane and EtOAc as eluents to give adduct 3a

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:
Article; Saito, Hikaru; Kanetake, Takayuki; Osaka, Kazuyuki; Maeda, Kousuke; Morita, Toshio; Yoshimi, Yasuharu; Tetrahedron Letters; vol. 56; 13; (2015); p. 1645 – 1648;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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. name: Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Step 1. Methyl l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclobutane-l -carboxylate: Into a 40 ml vial equipped with a magnetic stir bar and under N2 were added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2- dioxaborolane (2.26 g, 8.92 mmol), methyl l-(4-bromophenyl)cyclobutanecarboxylate (2 g, 7.43 mmol), Pd(dppf)C12, complex with DCM (307.18 mg, 371.56 muiotatauiotaomicron) and potassium acetate (2.19 g, 22.29 mmol). The vial was evacuated under vacuum and refilled with N2. DMF (15 mL) was added, and the mixture was degassed for 10 minutes with N2 and then heated to 100 C O/N. The black reaction mixture was cooled to RT, and purified by column chromatography through silica gel eluting with 100:0 to 0: 100 Hexanes:EtOAc as a gradient over 25 minutes. The desired fractions were combined, concentrated and further dried under high vacuum O/N to provide a yellow solid (1.6 g) LCMS (ESI+) m/z = 317 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1236357-65-5, its application will become more common.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 620-72-4 as follows. Quality Control of Phenyl 2-bromoacetate

To a solution of phenylbromoacetate (18.58 g, 86 mmol) in CH3CN under nitrogen was added a solution of (R)-phenylglycinol (10.17 g, 74 mmol) and di-isopropylethylamine (34 ml_, 195 mmol) in CH3CN. The volatiles were removed under reduced pressure keeping the bath temperature below 25 0C to obtain an oil that was treated with EtOAc (120 mL) and stirred for 15 min. The resulting white precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the desired product was isolated using column chromatography (SiO2) with a step gradient of 10 percent to 50 percent [v/v] EtOAc in cyclohexane to give after evaporation (f?)-5-phenylmorpholin-2- one EBE 06134 (3.17 g, 24 percent yield) as a white solid.MW: 177.2; Yield: 24 percent; White Solid; Mp (0C): 50.3Rf\ 0.30 (EtOAc:cyclohexane = 50:50). 1H-NMR (CDCI3, delta): 1.99 (s, 1 H, NH), 3.89 (q, 2H, J = 17.8 Hz, N-CH2), 4.18(dd, 1 H, J = 3.7 Hz, J = 10.3 Hz, 0-CH), 4.29 (t, 1 H, J = 10.5 Hz, N-CH), 4.40(dd, 1 H, J = 3.7 Hz, J = 10.5 Hz, 0-CH), 7.30-7.45 (m, 5H, ArH).13C-NMR (CDCI3, delta): 46.8, 54.8, 72.8, 125.3 (2xC), 127.0, 127.3 (2xC), 135.9,166.0. [G]22D = + 30.3 ¡ã (c = 1.00, MeOH).

According to the analysis of related databases, 620-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; WO2008/11478; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

Dimethyl 2-fluoromalonate (77.00g, 0.80mol, 2.0eq.) Was dissolved in 1L of tetrahydrofuran, cooled to -40 , 1M NaHMDS tetrahydrofuran solution (800mL, 0.80mol, 2.0eq. ), After stirring for 1h, add 400mL of a compound of formula (50g, 0.40mol, 1.0eq.) In tetrahydrofuran solution 400mL, return to room temperature after completion of the dropwise reaction for 2h, add 500mL of saturated ammonium chloride aqueous solution to separate, organic The phase was washed with saturated brine, dried, concentrated, column chromatography (petroleum ether / ethyl acetate), and concentrated to obtain 99.7 g of the compound of formula III, with a yield of 45.1%.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Zhang Leiliang; Xu Feng; (16 pag.)CN110963955; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics