Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 39520-24-6, name is Dimethyl 2-isobutylmalonate, 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 39520-24-6, category: esters-buliding-blocks

Taken 500mL four-necked flask was added 18.75g isobutyl-butyl malonate, 18.01g1,2,2,6,6- pentamethyl-piperidinol, 180g xylene, fitted with a reflux condenser, a thermometer, a stirrer and nitrogen, with stirring turn, was heated to 120 deg.] C, was added after 0.5h 0.48g dioctyltin oxide (first catalyst), the reaction continued at reflux for 6h, thin layer chromatography analysis showed that only the end of a significant point, transesterification . A flask was supplemented with 20g of xylene, and adding 26.15g2,6- butylated (dimethylaminomethyl) phenol (tradename antioxidant 703), and 0.41g lithium amide (second catalyst), raising the temperature to 145 deg.] C, the reaction was refluxed for 8h, TLC analysis showed that only a clear point, substitution reaction. After the heating was stopped and cooled to room temperature, the reaction mixture was added 3.5g of acetic acid, stirred for 30min, then the reaction solution was filtered dioctyltin oxide and lithium amide, washed 3 times with 70 water, water per 250ml, taken after the liquid separation the organic layer was recovered and the xylene distilled to give a tan solid which was recrystallized from ethanol and the crystals were washed, and dried to give 59.94g of light yellow powder, i.e., containing both a hindered phenol and a hindered amine structure weathering anti-aging agent. Product yield was 85.7% by HPLC analysis of purity of 94.15%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 2-isobutylmalonate, and friends who are interested can also refer to it.

Reference:
Patent; South China University of Technology; Rookie chemical (Yantai) Co., Ltd.; Cai, Zhiqi; Pi, Peng; Wenxiu, Fang; Lu, Yuan; (10 pag.)CN105294543; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 18469-52-8,Some common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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: To a solution of 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (1.0 equiv) in DMF was added HOBT (1.2 equiv) and EDCI (1.2 equiv), and the mixture was stirred for thirty minutes at room temperature. Triethylamine and corresponding 5a-5e was added, and then reaction was stirred for 8 h at room temperature. Then it was quenched by H2O. The mixture was washed with brine and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on a silica gel chromatography (petroleum ether/ethyl acetate = 1:1 to 1:20) to give corresponding products 6a-6e (yield 43%-62%) as white solid.

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

Reference:
Article; Liao, Chenzhong; Tian, Yongbin; Xie, Zhouling; Bioorganic and medicinal chemistry letters; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 625-56-9, name is Chloromethyl acetate, molecular formula is C3H5ClO2, 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 Chloromethyl acetate

Reference Example 15 A mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2-imidazolidinone (0.30 g) and chloromethyl acetate (1.35 g) was stirred for 24 hours at 100 C. The reaction mixture was concentrated under reduced pressure. The residue was subjected to ODS column chromatography (eluent: methanol/water=3/2) to give 4-acetoxymethyl-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium chloride (Compound 3, 45 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 2.08(3H,s), 3.61-4.08(4H,m), 4.65-4.75(1H,m), 4.86(1H,d,J=14 Hz), 5.11(1H,d,J=14 Hz), 6.07-6.20(2H,m), 6.69(1H,s), 6.96-7.05(1H,m), 7.25-7.36(2H,m), 7.82-7.95(5H,m), 8.78(1H,s), 9.06(1H,s), 10.46(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 625-56-9, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6583164; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Tert-butyl(chloro)diphenylsilane (18 ml, 68 mmol, GAS No 58479-61 -1) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, GAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, GAS No 16681 -56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, GAS No 1122-58-3) in DMF (81 ml), and the mixture was stirred at roomtemperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g SNAP cartridge, hexane/ethyl acetate gradient, 5% -> 30% ethyl acetate) to give the title compound (21 g).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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) 5-Benzyl-1H-[1,2,4]triazole-3-carboxylic acid butyl ester Ethyl-2-ethoxy-2-iminoacetate (1.318 g, 9.08 mmol) and phenyl acetic acid hydrazide (1.364 g, 9.08 mmol) were mixed together in ethanol (20 ml) and stirred at 80 C. for 1 h. Ethanol was evaporated. The residue was dissolved in n-butanol (20 ml). The reaction mixture was stirred at 150 C. for 20 h, then solvents were evaporated. The residue was suspended in acetonitrile and the precipitate was filtered off. The filtrate was purified by prep. HPLC (column: Interchrom C18 ODB, 10 um, 250*28 mm, 23 C.; A: water+0.1% HCOOH, B: ORG+0.1% HCOOH [ORG=methanol/acetonitrile 4:1]; gradient 20% B 2.5 min, 20-100% B in 35 min, 100% B for 2.5 min) to give the title compound. UPLC-MS (method F) Rt=0.85 min, [M+H]+=260.3; HPLC (method G) Rt=1.861 min.

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; NOVARTIS AG; US2012/35168; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H8BrNO2

A N2 degassed solution of methyl 2-amino-5-bromobenzoate (2.8 g) in 10 mL 1 pyridine was cooled to 0C before the drop wise addition of methane sulfonyl chloride (0.9 mL). The reaction mixture was stirred overnight at rt, then diluted with 50 mL ethyl acetate. The organic layer was washed with a saturated solution of Na2C03, with brine, then dried over MgS04 and evaporated to dryness (yield: 82%). LCMS (method B): 305.6 (M-H)” at 1.55 min.

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS TIERGESUNDHEIT AG; ELI LILLY AND COMPANY; GAUVRY, Noelle; TAHTAOUI, Chouaib; (57 pag.)WO2016/33341; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 14064-10-9, name is Diethyl 2-chloromalonate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H11ClO4

REFERENCE EXAMPLE 5a Ethyl 3-amino-4-cyclopropylfuran-2-carboxylate; To a solution of compound obtained in reference example 4a (5 g, 43.47 mmol) in DMF (108 ml_) was added diethyl chloromalonate (8.4 ml_, 52.17 mmol). The reaction mixture was stirred overnight at room temperature. After diluting with water (500 ml_), the reaction mixture was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4. After filtration, the filtrate was concentrated to dryness providing an orange syrup. The orange syrup was dissolved in ethanol (217 ml_) to which 1 ,5-diazabicyclo[4.3.0]non-5-ene (5.9 ml_, 47.8 mmol) was added, and the mixture was stirred at room temperature overnight. The solution was concentrated to dryness and the crude residue was purified by flash chromatography on silica gel using ethyl acetate and hexane mixtures of increasing polarity to afford 3 g of the title compound (yield: 65percent) as a light brown oil. LC-MS (Method 2): tR = 1.88 min; m/z 196 (MH+).

According to the analysis of related databases, 14064-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PALAU PHARMA, S. A.; WO2009/115496; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 535-11-5, name is Ethyl 2-bromopropionate, A new synthetic method of this compound is introduced below., Product Details of 535-11-5

(a) Methyl 3-(2-carbomethoxyethyl)thiopropionate To a solution of methyl mercapto propionate (66 g) in 51 ml of anhydrous methanol cooled at 0 C. was added 120 ml of a 25% solution of sodium methoxide in methanol. To this solution was added dropwise a solution of ethyl 2-bromopropionate (100 g) in 100 ml of anhydrous methanol. The reaction mixture was stirred at room temperature for 20 hours and the solvent removed. The oily residue was dissolved in 300 ml of ether and washed with sodium bicarbonate (10% solution). The organic layer was dried over MgSO4, filtered and the solvent removed, leaving a crude product which was used in the next step without further purification (see Swiss Patent No. 858012).

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; Lilly S.A.; Lilly Industries Limited; US5015656; (1991); A;,
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 431-47-0 as follows. Formula: C3H3F3O2

A. Preparation of N-propargyltrifluoroacetamide (43) Propargylamine (24.79 g, 0.450 mole; Aldrich, 99%) was added dropwise over 1 h to methyl trifluoroacetate (69.19 g, 0.540 mole, 1.2 eq, Aldrich) at 0. After stirring an additional hour at 0, distillation though a 15 cm Vigreux column afforded 62.12 g (91%) of trifluoroacetamide 43 as a colorless liquid (bp 68.5-69.5 at 11 torr). This material was homogeneous by NMR and GC and was used interchangeably with spectroscopically-identical material prepared by acylating propargylamine with trifluoroacetic acid anhydride. 1 H-NMR (CDCl3): 6.85 (broad s, 1H, NHTFA), 4.17 (dd, J=5.6 and 2.5, 2H, CH2), 2.35 (t, J=2.5, 1H, CH). IR (neat; cm-1): 3300 (N–H), 3095 and 2935 (C–H), 2130 (acetylene), 1720 (C=O), 1550 (N–H), 1430, 1365, 1160, 1040, 998, 918, 857, 829, 772, and 725.

According to the analysis of related databases, 431-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US5151507; (1992); A;,
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 25662-28-6 as follows. name: Methyl 1-cyclopentene-1-carboxylate

Example 1: Synthesis of compound of formula (IX) A solution of methyl- 1-cyclopentene-l -carboxylate (X) (10 mL, 81.88 mmol) in CH2C12 (200 mL) under N2 atmosphere is brought to 0C, and a solution of 1M DIBALH (diisobutylaluminium hydride) in hexane (204.7 mL, 204.7 mmol) is added drop by drop. The mixture is kept under stirring a 0C for 1 hour. H2O is added to the reaction, insolubles are filtered through celite, and the phases are separated. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated under low pressure. The pure compound of formula (IX) is obtained. Yield: 95% (7.62 g of a colourless liquid). Rf: 0.28 (EtPet/EtOAc 9: 1). ^- MR 400 MHz (CDC13) delta (ppm): 5.56 (s, 1H); 4.13 (s, 2H); 2.76 (bs, 1H); 2.30-2.26 (m, 4H); 1.90-1.82 (m, 2H). 13C-NMR 100 MHz (CDC13) delta (ppm): 143.67; 125.06; 61.60; 32.08; 31.86; 22.97. MS(ES+): m/z 121 [M+Na]+.

According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; TADDEI, Murizio; ATTOLINO, Emanuele; BALDUCCI, Evita; MICHIELETTI, Mario; WO2013/120871; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics