Month: October 2020

Adding some certain compound to certain chemical reactions, such as: 4341-76-8, name is Ethyl 2-butynoate, 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 4341-76-8. 4341-76-8

General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3¡¤H2O (2 ¡Á 5 mL), distilled water (5 mL), and acetone (2 ¡Á 5 mL) and reused in the next run. The filtrate was washed with water (2 ¡Á 10 mL) and brine (2 ¡Á 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Ethyl 2-butynoate.

Reference:
Article; Hu, Wenli; Yang, Weisen; Yan, Tao; Cai, Mingzhong; Synthetic Communications; vol. 49; 6; (2019); p. 799 – 813;,
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581065-95-4, These common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 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.

In the glove box under an atmosphere of dry nitrogen, a 3000 mL, 4-necked flask was charged with bis-CBZ-Lysine (200.0 g, 483 mmol), EDC (139 g, 724 mmol), and 1500 mL of 2:1 tetrahydrofuran:tert-butyl methyl ether. The flask was fitted with an immersion well; the remaining joints were stoppered, and the flask was transferred to the fume hood where one of the stoppers was replaced with an addition funnel connected by a gas inlet adapter to a bleed of dry nitrogen. The flask was placed in a salted ice-water bath, fitted with an overhead stirring apparatus, and stirred until 0[deg.] C. was attained. In the glove box under a dry nitrogen atmosphere, amino-dPEG(R)4-TBE (163 g, 507 mmol) was dissolved in tetrahydrofuran (170 ml). The PN10221 was then poured into the addition funnel under a nitrogen shower and added slowly by drop, keeping the temperature as close to [deg.] C. as possible. The reaction was allowed to continue overnight, warming slowly to ambient. The reaction appeared complete the next morning by TLC and RP-HPLC. Stirring of the reaction mixture was stopped, and the EDU was allowed to settle for several hours. The solution was then decanted from the EDU goo. The reaction solvent was removed by rotary evaporation under reduced pressure at 45[deg.] C. The residue was then dissolved in dichloromethane to a final volume of 1400 mL and washed once with 250 mL with 10% aqueous HCl, then once with 400 mL of 5% brine. The DCM was removed by rotary evaporation at 35[deg.] C., and the residue was dried by rotary evaporation at 45[deg.] C. under high vacuum for about 1 hour. Yield: 330 gms (95.4%) HPLC (AMINES3045FF METHOD): 96.2% purity by ELSD. TLC: Ethyl Acetate:Methanol 8:2. Major spot at Rf=0.69 with both UV quench at 254 nm and iodine-positive reaction. One minor UV quenching spot (no iodine reaction) near solvent front. No ninhydrin-positive spot. NMR: (400 MHz, CDCl3, [delta]): 7.322 (m, 11H, 2 CBZ rings & NH); 6.737 (s, 1H, amide); 5.762 (s, 1H, amide); 5.084 (m, 4H, 2*CH2O from CBZ); 4.153 (q, 1H, CHN on lysine); 3.526 (t, 2H, CH2 to N on lysine sidechain); 3.425 (t, 2H, CH2 [beta] to N on dPEG(R)); 3.164 (t, 2H, CH2N on PEG); 2.478 (t, 2H, CH2CO on PEG); 1.467 (m, 15H, lysine side chain alkyl methylene groups plus t-butyl ester). Quantitative NMR purity=96.8%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 581065-95-4.

Reference:
Patent; UNIVERSITY OF WASHINGTON; QUANTA BIODESIGN, LTD.; Davis, Paul D.; Wilbur, D. Scott; US2013/52130; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below.

A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at rt overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

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; Bradshaw, Curt; Bhat, Abhijit; Lai, Jing Yu; Doppalapudi, Venkata; US2008/166364; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9, Adding some certain compound to certain chemical reactions, such as: 35180-01-9, name is Chloromethyl isopropyl carbonate, 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 35180-01-9.

To a solution of anhydrous sodium iodide (6 g, 40 mmol ) in anhy. acetonitrile (20 mL) chloromethyl isopropyl carbonate (2.9 g, 19 mmol) in anhyd. acetonitrile (10 mL) was added dropwise over 20 min. The reaction mixture, covered with aluminum foil (protected from light) was stirred at room temperature overnight. The solid separated was filtered, washed with acetonitrile and the filtrate was concentrated under reduced pressure. Residue was dissolved in water (10 mL) and organics were extracted in ether (25 mL). Ether extracts were washed with sodium bisulfite (5%, 10 mL), later brine (10 mL). Organic layer was dried over anhd. sodium sulfate, filtered, concentrated and dried under high dried vacuum. Yield 2.72 g (58%); 1H-NMR delta 1.3 (d, 6H), 4.95 (m, 1H), 5.95 (s, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 35180-01-9.

Reference:
Patent; Iyer, Radhakrishnan P.; Padmanabhan, Seetharamaiyer; US2007/149462; (2007); 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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, A new synthetic method of this compound is introduced below., 61367-07-5

Example 19(1r,4R)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide Step 1. Preparation of (1r,4r)-methyl 4-(4-chloro-3-nitrophenylsulfonamido)cyclo hexanecarboxylate; (1r,4r)-methyl 4-aminocyclohexanecarboxylate HCl salt (7.75 g, 40 mmol) was suspended in a mixture of DCM (50 mL) and then treated with triethylamine (22.31 mL, 160 mmol), followed by 4-chloro-3-nitrobenzene-1-sulfonyl chloride (11.27 g, 44 mmol). The reaction mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aq. HCl (3¡Á100 mL), brine (100 mL) and dried over sodium sulfate. Filtration and concentration of the organic solution gave product (14.1 g) as a yellow solid (MS: (M+H)+=377.3).

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; NOVARTIS AG; US2012/28969; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 1731-86-8, name is Methyl undecanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1731-86-8

General procedure: The synthesis of the AKGs was performed following the literature with some modifications (Baumann and Mangold 1964; Hanus et al. 2001; Appendino et al. 2003; Parkkari et al. 2006). LiAlH4 (550 mg, 14.5 mmol) was added slowly to a solution of the corresponding methyl ester (3.4 mmol) in anhydrous tetrahydrofuran (15 mL) at 0C and stirred for 1 h and was then left at 20C for 20 h. The reaction mixture was washed with NaOH (10%) followed by HCl (10%) and extracted with diethyl ether (3 ¡Á 20 mL); the extract was neutralized with saturated NaHCO3, dried under reduced pressure and purified by CC. The alcohol obtained was subsequently mesylated in absolute pyridine (4.5 mL, 55.6 mmol) at 0C by the addition of MsCl (880 mg, 7.65 mmol) and the solution was maintained for 24 h at 20C. After quenching the reaction with 5 mL of degasified water, the solution was extracted with diethyl ether (4 ¡Á 20 mL). The organic phase was washed with H2SO4 (2 N), neutralized, concentrated in vacuo, and the crude mesylate was purified by CC. KOH (127 mg, 2.26 mmol) was added to the chiral precursor (R)-solketal (283 mg, 2.14 mmol) in anhydrous toluene (2 mL). The reaction stirred at 50C for 1 h before the addition of metallic Na (3 mg, 0.15 mmol) followed by the mesylate dissolved in toluene (15 mL), and the resulting mixture was kept at 50C for 72 h. The reaction was quenched with HCl (10%) and extracted with ethyl ether (4 ¡Á 20 mL). The organic phase was neutralized, concentrated and purified by CC to give 1-O-alkyl-2,3-O-isopropylidene-sn-glycerol. This intermediate was deprotected in 5 mL of HCl:MeOH (1:10 v/v) and refluxed overnight. After the addition of H2O (10 mL) and extraction with diethyl ether (4 ¡Á 20 mL), the organic phase was neutralized, evaporatedto dryness in vacuo, and the residue was purified by CC to afford pure AKGs. Each step in the synthesis was monitored by TLC, and all CC steps were eluted with hexane-toluene-ethyl acetate (10:0:0-0:10:0-0:0:10) mixtures. The structures of the synthesised compounds were confirmed by 1H, 13C APT NMR with COSY, HMQC, HMBC and ESI-MS or HRESI-MS spectra along with the specific optical rotation.

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, 1731-86-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fernandez Montoya, Deicy J.; Contreras Jordan, Luis A.; Moreno-Murillo, Barbara; Silva-Gomez, Edelberto; Mayorga-Wandurraga, Humberto; Natural Product Research; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1128-76-3, 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. 1128-76-3, name is Ethyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The following experimental procedure for the synthesis of morpholino(phenyl)-methanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18 mL, 2.1 mmol) and 10 mL THF. After cooling to 0 C, DIBALH (2.0 mL, 1.0 M in hexane, 2.0 mmol) was added dropwise and stirred for 3 h at same temperature. To a reaction mixture was slowly added ethyl benzoate (0.14 g, 1.0 mmol) and stirred for 10 min. The reaction was stopped by the aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2*10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded morpholino(phenyl)methanone (184 mg, 96%).

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

Reference:
Article; Jeon, Ah Ram; Kim, Min Eai; Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun; Tetrahedron; vol. 70; 29; (2014); p. 4420 – 4424;,
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. 6279-86-3, name is Triethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 6279-86-3

1b) 6-Hydroxy-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone; A mixture of the compound from example 1(a) (0.342 g, 1.63 mmol), triethyl methanetricarboxylate (0.755 g, 3.25 mmol), methanolic sodium methoxide (0.378 mL of a 4.37 M solution, 1.65 mmol) and ethanol (3 mL) was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and poured into 1M aqueous hydrochloric acid (20 mL). The mixture was extracted with ethyl acetate, and the extracts washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 5-10% methanol/dichloromethane) to give the title compound (0.320 g, 44%) as a foam. 1H NMR (400 MHz, DMSO-d6) delta ppm 5.05 (s, 2 H) 5.50 (s, 1 H) 6.87 (m, 2 H) 7.18-7.26 (m, 3 H) 7.36-7.43 (m,4H) 7.49 (m, 1 H) 11.64 (s, 1 H).

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:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1127-01-1, name is Ethyl 1-hydroxycyclohexanecarboxylate, 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 1127-01-1. 1127-01-1

1. Preparation of Hexylester: Example 1a with Modification (Column 125) 0.1 mol of ethyl-1-hydroxycyclohexanecarboxylate were introduced into 200 ml of absolute methylene dichloride, 0.12 mol of triethylamine (Et3N) were added, and a solution of 0.1 mol of 2-(2,4-dichlorophenyl)acetyl chloride in 50 ml of absolute methylene dichloride was added dropwise at 0-10 C. After the solution had been stirred for 16 h at room temperature, it was washed with aqueous citric acid and aqueous sodium bicarbonate solution, and the organic phase was dried over sodium sulfate and evaporated on a rotary evaporation.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Ethyl 1-hydroxycyclohexanecarboxylate.

Reference:
Patent; ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED; BRISTOW, James Timothy; (13 pag.)US2017/166546; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 25542-62-5, name is Ethyl 6-bromohexanoate, 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 25542-62-5. 25542-62-5

General Procedure 1: Preparation of Azides from Aliphatic BromidesAt RT, excess sodium azide (about 4-6 eq.) is added to a solution of the appropriate bromide in DMF (about 0.2 to 1 mol/l). The suspension is stirred vigorously at 50-80 C. for 2-18 h. After cooling to RT, the reaction mixture is diluted (for example with ethyl acetate or dichloromethane) and washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. After careful concentration under reduced pressure, the crude product may, if required, be purified by chromatography on silica gel (typical mobile phase mixture, for example, cyclohexane/ethyl acetate 100:1 to 10:1).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Ethyl 6-bromohexanoate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics