Month: May 2021

Some common heterocyclic compound, 16519-02-1, name is Diethyl 2-fluoro-2-methylmalonate, molecular formula is C8H13FO4, 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. Computed Properties of C8H13FO4

Diethyl 2-fluoro-2- methylmalonate (1 eq.) from the previous step was taken up in an aqueous pH=7.3 phosphate buffer (0.14 M, prepared by dissolving 7.3 g of NaHP04 and 2.1 g of KH2P04 per L of water). Lipase from Candida Rugosa (70 mg per mmol of substrate, 847 U/mg, Sigma Cat L1754) was then added and the resulting heterogeneous mixture was vigorously stirred at RT for 18 h. Depending on scale, occasional addition of 1 N NaOH was necessary to maintain the pH of the reaction mixture at -7.3 to ensure optimal activity. The reaction mixture was then added celite, stirred at RT for 1 h and filtered. The filtrate was extracted with EtOAc, dried over MgS04, and filtered. Concentration of the filtrate in vacuo furnished the desired product as a white, crystalline solid (71% yield, 93% enantiomeric excess).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16519-02-1, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (125 pag.)WO2017/49069; (2017); A1;,
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Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 tert-Butyl cyclopropanecarboxylate

Example 25ATert-Butyl 1-(prop-2-en-1-yl)cyclopropanecarboxylate 9.9 ml (70.32 mmol) of diisopropylamine were initially charged in 35 ml of THF, 28.1 ml (70.32 mmol) of a 2.5 M solution of n-butyllithium in n-hexane were added at -40 C. and the mixture was stirred for 30 min. The reaction mixture was then cooled to -78 C., and a solution of 10 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 5 ml of THF was added dropwise. The mixture was stirred at -78 C. for 4 h, and a solution of 5.8 ml (66.81 mmol) of allyl bromide in 5 ml of THF was then added dropwise. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully. The mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 10.7 g (83.5% of theory) of the target compound.GC-MS (Method 1): Rt=2.5 min; m/z=126 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta=5.82 (m, 1H), 4.98 (d, 2H), 2.21 (d, 2H), 1.37 (s, 9H), 0.99 (q, 2H), 0.69 (q, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87661-20-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
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These common heterocyclic compound, 141772-31-8, name is Methyl 5-amino-2-chloro-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. COA of Formula: C8H7ClFNO2

2. Preparation of Compound No. 18 A solution of 2-fluoro-4-chloro-5-methoxycarbonylaniline (1.0 g, 5 mmol) in THF (10 mL) was added dropwist to a solution of diphosgene (2.0 g, 10 mmol) in toluene (20 mL) with stirring at room temperature. The reaction mixture was stirred at room temperature for one hour and then heated to reflux for 4 hours. The mixture was then cooled to room temperature and the solvents were evaporated under reduced pressure to give 1.1 g of 2-fluoro-4-chloro-5-methoxycarbonylphenyl isocyanate as a solid.

The synthetic route of Methyl 5-amino-2-chloro-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; US6444615; (2002); B1;,
Ester – Wikipedia,
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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. 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8Br2O4

[Example 11] [Show Image] A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(10.6 g, 30.0 mmol) synthesized according to the method of a literature (Macromolecules, 1999, 32, 2455), Compound 15 (made by Sigma-Aldrich Corp.)(24.8 g, 66.0 mmol), PdCl2(dppf)·CH2Cl2 (2.45 g, 3.00 mmol), potassium carbonate (13.7 g, 13.7 mmol), water (60 mL) and THF (1.2 L) was refluxed under a nitrogen atmosphere for 16 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid, and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain Compound 16 (7.89 g, 15.0 mmol) in a yield of 50%. The physical properties of Compound 16 were as follows. 1H-NMR (CDCl3, delta ppm): 7.81 (s, 2H), 7.06 (d, 2H), 6.97-7.04 (m, 4H), 6.70 (d, 2H), 3.64 (s, 6H), 2.80 (t, 4H), 1.56-1.63 (m, 4H), 1.32-1.41 (m, 12H), 0.90 (t, 6H)

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; Sumitomo Chemical Company, Limited; EP2248818; (2010); A1;,
Ester – Wikipedia,
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Application of 39552-81-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39552-81-3, name is Methyl 2-(4-aminophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 100 9-Bromo-5-(p-methoxycarbonylmethylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and p-methoxycarbonylmethylaniline (215 mg, 1.3 mmol) to give 395 mg of the title compound (81%): mp 262 C. (dec); 1 H NMR (270 MHz, DMSO-d6) delta10.02 (s, 1H), 7.50 (d, 2H, J=8.3 Hz), 7.23 (bs, 1H), 7.18 (d, 2H, J=8.3 Hz), 7.17 (bs, 1H), 5.17~5.26 (m, 1H), 3.61~3.62 (m, 5H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.84 (dm, 1H, J=17.1 Hz),2.56~2.66 (m, 2H), 2.11 (dm, 1H, J=13.5 Hz), 1.76~1.94 (m, 1H).

The synthetic route of Methyl 2-(4-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; US5616586; (1997); A;,
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Related Products of 2672-58-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 1,3,5-Tris(hydroxymethyl)benzene A solution of trimethyl 1,3,5-benzenetricarboxylate (8.83 g, 0.035 M; Aldrich) in THF (125 mL) is added dropwise over a period of 45 minutes to a stirred mixture of lithium aluminum hydride (3.98 g, 0.105 M) and dry THF (150 mL) under a nitrogen atmosphere. The initial phase of the addition results in vigorous reaction and consequently the addition is very slow at first. As the ester solution is added, an orange mass forms when the drops came in contact with the LiAlH4 mixture. A yellowish-green mixture results and is stirred at room temperature. The excess LiAlH4 is quenched carefully by the addition of ethyl acetate and the resulting mixture is acidified with aqueous 2N HCl solution until the pH is <3 and aluminum salts have dissolved. The layers are separated and the aqueous layer is extracted 3 times with additional ethyl acetate and then with methylene chloride. The organic extract layers are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give a white solid (2.98 g, 51%). Recrystallization from acetonitrile-methylene chloride gives the title compound as white crystals (1.13 g) which appear to be hygroscopic when collected by suction filtration. The crystals are dried several days over P2 O5 in a vacuum desiccator after which they have amp of 76.5-78 C. 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, Trimethyl benzene-1,3,5-tricarboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; The Upjohn Company; US5500417; (1996); A;,
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Electric Literature of 2459-25-8, The chemical industry reduces the impact on the environment during synthesis 2459-25-8, name is Methyl 2-naphthoate, I believe this compound will play a more active role in future production and life.

4a (1.54 g, 9 mmol) was dissolved in 30 ml of ethanol, hydrazine hydrate was added, and the reaction was refluxed overnight. The next day, TLC monitored the reaction completely. At room temperature, a yellow solid precipitated continuously. Concentrate to a small volume, ice bath for 30 minutes, and filter to obtain a solid. Drying gave 1.21 g of a yellow solid. Yield: 72%.

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 2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University; Chen Jianzhong; Yang Bo; He Qiaojun; Pan Youlu; Ying Meidan; (29 pag.)CN108329232; (2018); A;,
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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. 63746-12-3, name is Dimethyl 4-aminoisophthalate, A new synthetic method of this compound is introduced below., Quality Control of Dimethyl 4-aminoisophthalate

To a mixture of (4-adamantan-1-yl-phenoxy)-acetic acid (229 mg, 0.8 mmol) and 4-aminoisophthalic acid dimethyl ester (301 mg, 1.4 mmol) were dissolved in DMF (5 mL), and EDCHCl (140 mg, 0.75 mmol), HOAt (163 mg, 1.2 mmol) and DIPEA (0.21 ml, 1.2 mmol) was added. The mixture was stirred overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=50:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl ester as a white solid (281 mg, 76.3% yield). 1H-NMR (CDCl3, 300 Hz) 12.00 (1H, s, NH), 9.40 (1H, d, J=1.8 Hz, aromatic), 8.12 (1H, d, J=7.8 Hz, aromatic), 7.78 (1H, dd, J=8.1 & 1.8 Hz, aromatic), 7.33 (2H, m, aromatic), 7.03 (2H, m, aromatic), 4.65 (2H, s, OCH2CO), 3.97 (3H, s, OCH3), 3.95 (3H, s, OCH3), 2.09 (3H, m, adamantyl), 1.89-1.90 (6H, m, adamantyl), 1.72-1.82 (6H, m, adamantyl).

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; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 25415-67-2, 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. 25415-67-2, name is Ethyl 4-methylpentanoate, This compound has unique chemical properties. The synthetic route is as follows.

Tetrahydrofuran (35 ml) was cooled down to -70C under inert gas atmosphere. At this temperature, 4.44 ml (11.1 mmol) of n-butyllithium solution (2.5 M in hexanes) and then 0.51 ml (9.71 mmol) acetonitrile were added dropwise. After 3 min at -70C, 1 .1 5 ml (6.93 mmol) ethyl 4- methylpentanoate were added dropwise at such a rate that the temperature of the solution did not exceed -66C. The mixture was stirred for 2 h at -45C before 22.2 ml of 1 N hydrochloric acid were added dropwise. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with diethyl ether. After filtration through silica gel, the filtrate was evaporated under reduced pressure to yield 1.05 g of the crude title compound, which was used in the next step without further purification.GC-MS (method 5): Rt = 3.23 min; MS (EIpos): m/z = 138 (M-H)+ ‘H-NMR (DMSO-dg): delta = 4.03 (s, 2H), 2.51 (t, 2H), 1.50 (sext, 1H), 1.38 (q, 2H), 1.35 (d, 6H) ppm.

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

Reference:
Patent; Bayer Schering Pharma AG; MICHELS, Martin; FOLLMANN, Markus; VAKALOPOULOS, Alexandros; ZIMMERMANN, Katja; TEUSCH, Nicole; LOBELL, Mario; ENGEL, Karen; WO2011/42367; (2011); A1;,
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Ester – an overview | ScienceDirect Topics

Reference of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, molecular formula is C9H9BrO2, 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-Bromo-4-methoxycarbonylbenzoic acid[0095] 2-bromo-4-methylbenzoic acid methyl ester (10.00 g, 42.8 mmol), tetrabutyl ammonium bromide (345 mg, 0.86 mmol), ruthenium chloride trihydrate (86 mg, 0.43 mmol), dichloroethane (14 mL) and sodium hypochlorite 10% (115 mL) were mixed. The pH at the aqueous phase was adjusted to 9.0 by addition of 20% v/v H2SO4. The biphasic mixture was stirred for 2.5 hours, and meanwhile, NaOH 20% v/v was added to keep the pH at 9. The phases were separated and the aqueous phase was washed with DCM (3 × 50 mL), acidified with 20% H2SO4 and extracted with EtOAc (3 × 50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford 3-bromo-4-methoxycarbonylbenzoic acid as a whitish solid (2.33 g, 21% yield). 1H-NMR (400 MHz, CDCl3): 8.38 (d, J = 1.5, 1H), 8.07 (dd, J = 8.1, 1.6, 1H), 7.84 (d, J = 8.1, 1H), 3.98 (s, 3H).

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-bromo-4-methylbenzoate, its application will become more common.

Reference:
Patent; Prous Institute for Biomedical Research, S.A.; Prous, Josep R.; Serradell, Neus; Munoz, Rosa; Flores, Ramon; Garcia-Delgado, Noemi; EP2573088; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics