Esters-buliding-blocks

Synthetic Route of 5121-34-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5121-34-6 name is Methyl 2-amino-3-methoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[Step b] To a solution of compound 2 (86.7 g, 473 mmol) in N,N-dimethylformamide (430 mL) was added N-bromosuccinimide over 15 min under ice-cooling, and the mixture was stirred for 1 hr. To the reaction solution were added saturated aqueous sodium hydrogen carbonate solution (500 mL) and water (500 mL), and the mixture was extracted with ethyl acetate (1.0 L). The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, and suspended and washed in n-hexane (120 mL) to give compound 3 (108 g, 88.1 %). 1H-NMR (400 MHz, CDCl3)delta: 3.87(6H, s), 6.03(2H, brs), 6.90(1H, d, J=2.0Hz), 7.26(1H,s), 7.60(1H, d, J=2.4Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); A1;,
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Reference of 59247-47-1, 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. 59247-47-1, name is tert-Butyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[l-cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5- yl]methoxy]-2-azabicyclo[2.2.1]heptane 621 (45 mg, 0.12 mmol, 1.00 equiv.), toluene (20 mL), tert-butyl 4-bromobenzoate (45.7 mg, 0.18 mmol, 1.50 equiv), BINAP (15 mg, 0.02 mmol, 0.20 equiv.), Cs2CO3 (116 mg, 0.36 mmol, 3.00 equiv.), and Pd2(dba)3 (11 mg, 0.01 mmol, 0.10 equiv.). The resulting mixture was heated for at 1 10¡ãC for 2 days. After cooling to room temperature, solids were filtered out, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 10 to 1 :5, and to 1 :3). Removal of solvents afforded tert-butyl 4-[(1S,4S,5R)-5-[[l- cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan- 2-yl]benzoate 70a (40 mg, 61percent) as a light brown oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5326-50-1, name is Ethyl 2-(1-hydroxycyclohexyl)acetate, 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 5326-50-1, name: Ethyl 2-(1-hydroxycyclohexyl)acetate

To a solution of X4 (510 mg) in MeOH was added IN aqueous NaOH. The reaction mixture was stirred at 600C for Ih5 and then concentrated in vacuo. The residue was diluted with water, washed with Et2O and the aqueous layer acidified with IN aqueous citric acid and extracted with EtOAc. The organics were dried (MgSO4) and concentrated in vacuo to yield after recrystallization compound X5 (220mg): 1H-NMR (CDCl3, 500MHz) 3.63 (s, IH), 2.45 (s, 2H), 1.22-1.64 (m, 10H) ppm; FIA m/z 157.2 ES”.

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, Ethyl 2-(1-hydroxycyclohexyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/25307; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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 LiAlH4 (1.35g, 35.5mmol, 1.5equiv.) in dry Et2O (13.0mL) under argon atmosphere was added dropwise a solution of AlCl3 (2.22g, 16.6mmol, 0.7equiv.) in dry Et2O (6.5mL). After 20min of stirring at 0C, a solution of ethyl (E)-4,4,4-trifluorocrotonate (4.00g, 23.8mmol, 1.0 equiv.) in dry Et2O was added dropwise. The resulting mixture was allowed to stir at 0C for 2 h. A saturated aqueous solution of Na2SO4 was then added (Caution: very exothermic reaction). The mixture was filtrated and the solid was washed several times with Et2O. The organic layers were combined and washed with brine and dried over MgSO4. Solvent was removed by thorough distillation at atmospheric pressure to afford (E)-4,4,4-trifluorobut-2-en-1-ol (7) as a colorless oil which was used without any further purification.

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

Reference:
Article; Forcellini, Elsa; Hemelaere, Remy; Desroches, Justine; Paquin, Jean-Francois; Journal of Fluorine Chemistry; vol. 180; (2015); p. 216 – 221;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 431-47-0, These common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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.

Phthalimide (100 mg, 0.68 mmol), DMSO (10 mL), CH3ONa (112 mg, 2 mmol, 3 eq.) was added to the reaction flask in turn, stirred at room temperature for 5 minutes, and then uniformly dispersed after NaH. Methyl trifluoroacetate (0.28 mL, 2.7 mmol, 4 eq.) was slowly injected into the reaction flask. After reacting for 10 hours, the TLC was plated, and the starting point disappeared, that is, the reaction was completed, and the stirring was stopped. Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution. The organic phases were combined, and the organic phase was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography gave white solid N-methylphthalimide (109 mg,Yield 100%).

The synthetic route of 431-47-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 94994-15-7, These common heterocyclic compound, 94994-15-7, name is Methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, 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 solution of 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (108 mg, 0.545 mmol), methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-l-carboxylate (90 mg, 0.454 mmol) and triphenylphosphine (179 mg, 0.681 mmol) in toluene (2 mL) at 0 C was added (¡ê)-di-tert-butyl diazene-l,2-dicarboxylate (157 mg, 0.681 mmol) in toluene (0.5 mL) slowly. The reaction mixture was stirred at room temperature for 5 min and the reaction mixture was heated to 90 C for 18 hours. After cooled to room temperature, dichloromethane (5 mL) and water (5 mL) were added to the reaction mixture. The layers were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated in vacuo to afford the crude. This crude was purified by preparative HPLC (PHENOMENEX Axia 5 muiotaeta C18 30 x 100 mm column; detection at 220 nm; flow rate = 40 mL/min; continuous gradient from 30% B to 100% B over 10 min + 5 min hold time at 100% B, where A = 90: 10:0.1 H20:MeOH:TFA and B = 90: 10:0.1 MeOH:H20:TFA) to give the title compound (75 mg, 41.5% Yield; 95% pure by LC/MS) as a light yellow oil. [M+Na]+ = 401, pi MR (400 MHz, CDC13) delta 6.70 (dd, J= 14.3, 1.6 Hz, 2H), 3.65 (s, 3H), 3.63 (s, 2H), 2.96 (s, 2H), 1.86 – 1.77 (m, 6H), 1.59 – 1.55 (m, 6H), 1.48 (s, 6H).

The synthetic route of 94994-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; ZHANG, Hao; CHENG, Peter T.W.; TAO, Shiwei; WO2014/159802; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 175867-59-1, name is Methyl 4-aminocyclohexanecarboxylate, molecular formula is C8H15NO2, 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: C8H15NO2

EXAMPLE 23(1) 2-[4-(Methoxycarbonyl)cyclohexylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (381 mg) was obtained from 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (300 mg) and methyl 4-amino-1-cyclohexanecarboxylate (222 mg) in a manner similar to Example 1(1). NMR (CDCl3, delta): 1.70-2.03 (8H, br), 2.52 (1H, br), 3.63 (1H, br), 3.71 (3H, s), 4.50 (2H, d, J=7 Hz), 5.97 (2H, s), 6.41 (1H, br), 6.66 (1H, m), 6.78-6.87 (3H, m), 8.14 (1H, m), 8.30 (1H, m), 8.86 and 9.08 (1H, br); Mass m/z: 456(M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175867-59-1, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6384080; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 14064-10-9, These common heterocyclic compound, 14064-10-9, name is Diethyl 2-chloromalonate, 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.

4-[4-amino-5-(ethoxycarbonyl)furan-3-yl]piperazine-1-carboxylate tert-Butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate (2.35 g, crude product), diethyl chloromalonate (1.94 g, 10 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.56 g, 30 mmol) were dissolved in tetrahydrofuran (20 mL), followed by stirring at room temperature overnight. Water was added to the reaction liquid, followed by extraction with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel column chromatography (hexane:ethyl acetate=6:1?2:1) to give tert-butyl 4-[4-amino-5-(ethoxycarbonyl) furan-3-yl]piperazine-1-carboxylate (1.30 g, 38percent, 2 steps) as a yellow solid. 1H-NMR (CDCl3) delta: 1.38 (3H, t, J=7.1 Hz), 1.47 (9H, s), 1.87-1.95 (2H, m), 2.38-2.49 (1H, m), 2.74-2.87 (2H, m), 4.10-4.28 (2H, m), 4.35 (2H, q, J=7.1 Hz), 4.50 (2H, brs), 7.06 (1H, s).

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA CO., LTD.; Morimoto, Toshiharu; Koshizawa, Tomoaki; Watanabe, Gen; Ohgiya, Tadaaki; Yamasaki, Nao; Inoue, Noriyuki; US2013/102621; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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.

General procedure: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 ¡Á 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 ¡Á 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].6-Phenylpyridin-2(1H)-one (13a)By following the general procedure, the reaction of PhCN (5a;201 mg, 1.94 mmol) with crotonate 12 (374 mg, 1.94 mmol) inthe presence of Zn (252 mg, 3.88 mmol) and TMSCl (7 mg, 3 mol%) in 1,4-dioxane (6 mL) for 4 h, followed by hydrolysis with 50%aq K2CO3 (5 mL) gave a light-yellow solid; yield: 205 mg (62%);mp 194-195 C; Rf = 0.5 (hexanes-EtOAc, 2:1).IR (KBr): 2904, 1643, 1612, 1550, 1493, 990, 921, 795, 761 cm-1.1H NMR (400 MHz, CDCl3): delta = 12.49 (br s, 1 H), 7.72 (d, J = 6.9Hz, 2 H), 7.59-7.40 (m, 4 H), 6.55-6.47 (m, 2 H). 13C NMR (100MHz, CDCl3): delta = 165.4, 147.1, 141.5, 133.6, 130.1, 129.2, 126.8,118.7, 105.0. HRMS (ESI): m/z [M + H] calcd for C11H9NO:172.0762; found: 172.0750.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H10O3

Triphenylphosphine (538 mg, 2.05 mmol) was added to a solution of quinazolin-8-ol (250 mg, 1 .71 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (245 mg, 1 .88 mmol) was added, followed by DIAD (0.40 mL, 2.1 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 2 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc: EtOH (3:1 ) in hexanes gradient to give the title compound (178 mg, 40%) as a light brown oil. 1H NMR (400 MHz, CDCI3) delta 2.65-2.75 (m, 2 H), 2.80-2.90 (m, 2 H), 3.20-3.28 (m, 1 H), 3.74 (s, 3 H), 5.10-5.15 (m, 1 H), 7.04-7.08 (m, 1 H), 7.47-7.57 (m, 2 H), 9.35-9.37 (m, 2 H); LC-MS (LC-ES) M-H = 258.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics