Month: September 2021

Application of 541-16-2, These common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, 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 mixture of di-tert-butyl malonate (4.3 g, 19.91 mmol, 1.99 equiv) and potassium carbonate (2.8 g, 20.29 mmol, 2.03 equiv) in N,N-dimethylformamide (30 mL) was stirred at 65C for 30 min. A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol- 2-yl)benzoate (2.65 g, 10.00 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) was then added dropwise with stirring to the reaction mixture. The resulting solution was stirred at 65C overnight and then quenched with 60 mL of ice and water. The mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 4.0 g (90%) of methyl 4-(4-(3-tert-butoxy-2-(tert- butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate as a light yellow solid. LC-MS: (ES, m/z): 446 [M+H]+, 390, 334, 272, 230, 115.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; RUGA CORPORATION; GIACCA, Amato; LAI, Edwin; RAZORENOVA, Olga; CHAN, Denise; HAY, Michael, Patrick; BONNET, Muriel; SUN, Connie; TABIBIAZAR, Ray; YUEN, Po-wai; WO2013/155338; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 57486-67-6,Some common heterocyclic compound, 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

Sodium hydride (1427 g, 35.7 mmoi) was added to a solution of methyl 2-(-fiuorophenyl)acetate(2 g, 1189 mmoi) in TIfF (20m1) at 0 C and allowed to stir at same temperature for 30 mi Methyliodide (5.21 ml, 83 mrnoi) was added dropwise and reaction mixture was stirred at RT for overnight. The reaction mixture was neutralized with saturated ammoniurn chloride and extracted with ethyl acetate (2x150m1). Combined organic phase was washed with brine, dried with anhydrous sodium sulfate and evaporated to give methyl 2-( -fluorophenyl)-2-methyipropanoate (1.5 g, 7.64 mrnol, 64.3 % yield) as oil.

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-(2-fluorophenyl)acetate, its application will become more common.

Reference:
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 64123-77-9, name is Methyl 2-(3-fluorophenyl)acetate, 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. Safety of Methyl 2-(3-fluorophenyl)acetate

General procedure: The oil was thendissolved in EtOH, and NH2NH2.H2O (3 eq) was added.The mixture was refluxed for 10 h. CH2Cl2 (30 mL) was thenadded and extracted with distilled H2O (3 × 20 mL). Theorganic phase was separated, dried on anhydrous Na2SO4,and evaporated under vacuum to afford correspondinghydrazide 7a in very good yield (white solid, 1.02g, 93%)

The synthetic route of Methyl 2-(3-fluorophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vu, Vu Van; Nhung, Trinh Thi; Thanh, Nguyen Thi; Chinh, Luu Van; Tien, Vu Dinh; Thuy, Vu Thu; Thi Thao, Do; Nam, Nguyen Hai; Koeckritz, Angela; Vu, Tran Khac; Journal of Chemistry; vol. 2017; (2017);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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. Quality Control of Methyl 2,2-dimethoxyacetate

Cyclohexanone Compound 2a (1.37 g, 14.0 mMol) in THF (5 mL) was added dropwise to a solution of LHMDS (16.0 mL, 16.0 mMol) in anhydrous THF (25 mL) at -78 C. under a N2 atmosphere. The solution was stirred at -78 C. for about 1 hr. Methyl dimethoxyacetate Compound 11a (1.88 g, 14.0 mMol) in anhydrous THF (5 mL) was then added dropwise. The reaction mixture was stirred while warming to r.t. over a period of about 15 hrs, then the reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford 2-(2,2-dimethoxy-acetyl)-cyclohexanone Compound 11b (1.82 g, 65%). Benzylhydrazine dihydrochloride Compound 11c (1.75 g, 9.00 mMol) and K2CO3 (1.51 g, 10.92 mMol) were added to a solution of Compound 11b (1.80 g, 9.10 mMol) in MeOH (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred overnight while warming to r.t., then the reaction was quenched with water (20 mL). The organic layer was diluted with EtOAc (200 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 20% EtOAc in hexane) to afford 1-benzyl-3-dimethoxymethyl-4,5,6,7-tetrahydro-1H-indazole Compound 11d (1.80 g, 70%) as a colorless oil. 3N HCl (8 mL) was added to a solution of Compound 11d (1.70 g, 5.9 mMol) in acetone (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred for 4 hrs while warming to r.t., then the reaction was quenched with water (20 mL), neutralized to pH 7 with K2CO3 and diluted with CH2Cl2 (100 mL). The organic layer was washed with water and brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford a 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e (1.35 g, 95%) as a colorless oil. Methanesulfonyl chloride Compound 11f1 (2.0 g, 17 mMol) and TEA (2.43 mL, 17.46 mMol) were added to a solution of (1R)-1-phenyl-ethylamine Compound 11f2 (1.75 g, 17.5 mMol) in CH2Cl2 (50 mL) at 0 C. under a N2 atmosphere. The mixture was stirred for 3 hrs while warming to r.t., then the reaction was quenched with water (5 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford the corresponding N-(1-phenyl-ethyl)-methanesulfonamide Compound 11f3 as an oil. (Boc)2O (di-tert-butyldicarbonate) (4.57 g, 21.0 mMol) and DMAP (8 mg) were added to a solution of the methanesulfonamide Compound 11f3 in CH2Cl2 (10 mL) at 0 C. under a N2 atmosphere. The mixture was stirred overnight while warming to r.t., then the reaction was quenched with a saturated solution of NaHCO3 (sodium bicarbonate) (10 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude Boc-protected methanesulfonamide product. The product was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f (3.89 g, 80%) as a colorless oil. Adapting a published procedure (Tozer M J, Woolford A J A and Linney I A, Synlett, 1998, 2, 186-188) to obtain the target compound, a 1M solution of KOtBu (potassium tert-butoxide) in THF (0.75 mL, 0.75 mMol) was added dropwise to a solution of the ester Compound 11f (0.070 g, 0.250 mMol) in anhydrous THF (5 mL) at -78 C. under a N2 atmosphere. After 45 min, Compound 11e (0.060 g, 0.250 mMol) diluted in THF (3 mL) was added dropwise. The solution was reacted over a 15 hr period while warming to ambient temperature. The reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. The product was purified by flash chromatography (eluted with 20% EtOAc in hexane) to give Compound 260 (0.079 g (75%), as a white solid. MS m/z 422 (MH+); 1H NMR (CDCl3, 400 MHz) delta 7.56 (d, J=15.5 Hz, 11H), 7.35-7.19 (m, 8H), 7.11-7.09 (m, 2H), 6.42 (d,J=15.5 Hz, 1H), 5.21 (s, 2H), 4.61-4.11 (m, 2H), 2.45-2.41 (m, 2H), 2.36-2.33 (m, 2H), 1.75-1.67 (m, 4H), 1.55 (d, J=6.5 Hz, 3H).

The synthetic route of Methyl 2,2-dimethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lagu, Bharat; Liotta, Fina; Pan, Meng; Wachter, Michael P.; Xia, Mingde Xia; US2005/228034; (2005); 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 344-14-9 as follows. Computed Properties of C5H7FO4

A mixture of 2-fluoro-4-amidinopyridine hydrochloride (1.17 g, 6.662 mmol), dimethyl fluoromalonate (1 g, 6.662 mmol), DBU (3.35 mL, 22.4 mmol) and MeOH (50 mL) was stirred at room temperature overnight. The crude reaction mixture was evaporated under reduced pressure to yield a brown oil. A 2 N HC1 solution was cautiously added and the precipitate was collected by filtration, washed with water and dried in a vacuum oven to give the title compound (0.992 g, 66% yield). LCMS: RT 2.91 min, MI 225, Method (4LCMS1).

According to the analysis of related databases, 344-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1139-13-5,Some common heterocyclic compound, 1139-13-5, name is Diethyl cyclohexane-1,1-dicarboxylate, molecular formula is C12H20O4, 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 1. To a solution of compound 18-1 (4.0 g, 17.5 mmol) in EtOH (20 mL) was added 85% aqueous KOH solution (1.15 g, 17.5 mmol) at r.t. After the reaction mixture was stirred at 76 C for 3 h, it was concentrated and partitioned between EtOAc (15 mL) and H20 (25 mL). The aqueous phase was acidified with IN HC1 to pH = 3 and extracted with EtOAc (15 mL x 2). The organic layer was concentrated to give compound 18-2 as an oil (2.5 g, yield: 71.4%). ‘H NMR (400 MHz, CDC13) delta 4.20 – 4.15 (m, 2 H), 2.03 – 1.90 (m, 4 H), 1.56 – 1.47 (m, 6 H), 1.45 – 1.43 (t, 4.0 Hz, 3 H).

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

Reference:
Patent; GENENTECH, INC.; THE UNIVERSITY OF AUCKLAND; LEE, Ho Huat; TERCEL, Moana; FLYGARE, John A.; GUNZNER-TOSTE, Janet; PILLOW, Thomas H.; SAFINA, Brian; STABEN, Leanna; VERMA, Vishal; WEI, BinQing; ZHAO, Guiling; WO2015/95227; (2015); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, 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.

A mixture of 121A (2.28 g, 10.0 mmol) and N-bromosuccinimide (1.96 g, 11.0 mmol) in carbon tetrachloride (20 mL) was deoxygenated with a flow of nitrogen for 5 min. 2,2′-Azobisisobutyronitrile (82 mg, 0.5 mmol) was added and the mixture was refluxed for 18 h. Hexanes was added to the cooled mixture, and the resulting solid was filtered and washed with hexanes. The filtrate was concentrated on a rotary evaporator and then chromatographed (silica gel, step gradient from 100% hexanes to 5% ethyl acetate in hexanes) to give 121B (1.3 g, 42%) as clear oil. LC-MS m/z: 309.1 (M+H)+.

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-(3-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

To a stirred solution of methyl 4-bromo-3-methylbenzoate (5g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and morpholine (2.3 g, 26 mmol). The mixture was degassed for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title compound as a yellow solid (4.3 g, 84%). 1H NMR (CDCI3, 400 MHz) delta 7.86-7.90 (m, 2H), 7.13-7.16 (d, 1 H), 3.98-4.0 (m, 4H), 3.91 (3H, s), 3.10-312 (m, 4H), 2.45 (3H, s). LC/MS (Method A): 236.0 (M+H)+. HPLC (Method B) Rt 2.24 min (Purity: 95.3%).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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. 1459-93-4, name is Dimethyl isophthalate, A new synthetic method of this compound is introduced below., COA of Formula: C10H10O4

In a 3-necked 500 mL round-bottomed flask equipped with a mechanical stirrer was placed dimethyl isophthalate (20.00 g, 0.103 mol, 1 eq.) dissolved in acetone (200 mL). To this mixture was added dropwise over 20 min a sln of NaOH (4.33 g, 0.108 mol, 1.05 eq.) in MeOH (40 mL). The resulting milky suspension was stirred at r.t. overnight. Then, another portion of NaOH (0.433 g, 0.011 mol, 0.1 eq.) was added into the reaction and the suspension was stirred for another 5 hours. The solvent was removed under vacuum and the white precipitate thus obtained was dissolved in water (400 mL). Concentrated HCl (15 mL) was added dropwise until pH~1. Then, the suspension was filtered; the collected precipitate was washed with water (4×100 mL) and dried under vacuum at 65C for 24 hours to give white solid 18.25 g. The obtained monomethyl isophthalate was used directly without further purification. In a 3 necked 500 mL round-bottomed flask equipped with a magnetic stirrer and a low temperature thermometer under a nitrogen atmosphere was placed monomethyl isophthalate (5.00 g, 0.027 mol, 1 eq.) dissolved in dry THF (125 mL). Then, this solution was placed in an ice-water bath and a solution of BH3?SMe2 (2M in THF, 70 mL, 0.14 mol, 5 eq.) was added dropwise slowly over 90 min to maintain the temperature in the solution below 7C. After another 15 min, the cooling bath was removed and the solution was allowed to reach ambient temperature. After 5 hours, the reaction was carefully quenched (strong gas evolution) with small pieces of ice while cooling in an ice-water bath. When the gas evolution ceased, brine (50 mL) was added and the resulting mixture was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with diluted bleach (50 mL, original solution 9.6% bleach diluted 10 times), brine (50 mL) and dried (MgSO4). The solvent was removed under vacuum to give an oil which contained a small amount of white precipitate. Diethyl ether (20 mL) was added and the solid was removed by filtration and washed with Et2O (2×10 mL). The filtrate was concentrated to yield a pale yellow oil (4.48 g). The crude oil was then purified by silica gel column chromatography (PE:EA, 4:1 to 7:3) to afford methyl 3-hydroxymethylbenzoate (2d) as colorless oil (3.77 g, 82%). Rf = 0.17 (EtOAc:PE = 1:4); 1H NMR (300 MHz, CDCl3), delta (ppm): 8.00 (s, 1H, HAr), 7.93 (dt, J = 7.7, 1.4 Hz, 1H, HAr), 7.61 – 7.51 (m, 1H, HAr), 7.40 (t, J = 7.7 Hz, 1H, HAr), 4.71 (s, 2H, OCH2), 3.89 (s, 3H, OMe).

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:
Article; Wang, Shuai; Lafont, Dominique; Rahkila, Jani; Picod, Benjamin; Leino, Reko; Vidal, Sebastien; Carbohydrate Research; vol. 372; (2013); p. 35 – 46;,
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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 24807-40-7

To a solution of dimethyl methylphosphonate (1.16 g, 9.33 mmol) in THF (12.5 mL, 0.25 M) at -78 C was added nBuLi (3.9 mL, 9.33 mmol, 2.5 M in hexane). The mixture was stirred for 30 min after which a THF solution (2.5 mL) of ester 11 (750 mg, 3.10 mmol) was added slowly. The reaction mixture was warmed to RT and let stir for 1h, upon which time TLC indicated complete consumption of 11. The reaction mixture was quenched with saturated aqueous NH4Cl (5 mL). The mixture was diluted with H2O (10 mL) and extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with H2O (50 mL), saturated aqueous NaCl (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by FCC (EtOAc) yielded 12 (1.09 g, 3.01 mmol, 97%) as a clear oil. Data for 12: Rf 0.45 (1:1 Hexanes: EtOAc); IR (thin film) 3034, 2955, 1714, 1512, 1244 cm-1; 1H NMR (700 MHz, CDCl3) delta 7.44 (d, J = 7.5 Hz, 2 H), 7.39 (t, J = 7.6 Hz, 2 H), 7.34 (t, J = 8.6 Hz, 2 H), 6.91 (d, J = 8.6 Hz, 2 H), 5.05 (s, 2 H), 3.76 (d, J = 11.3 Hz, 6 H), 3.08 (d, J = 22.7 Hz, 2 H), 2.94 (t, J = 7.2 Hz, 2 H), 2.87 (t, J = 7.2 Hz, 2H); 13C NMR (176 MHz, CDCl3) delta 201.1, 157.2, 137.1, 132.9, 129.4, 128.6, 127.9, 127.5, 114.9, 70.0, 53.1 (d, J = 6.3 Hz), 45.8, 41.6 (d, J = 128.0 Hz), 28.6; HRMS (ESI) calcd for C19H24PO5 [M+H]: 363.1357, found 363.1361.

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:
Article; Salih, M. Quamar; Beaudry, Christopher M.; Tetrahedron Letters; vol. 58; 21; (2017); p. 2023 – 2025;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics