Tag: M.W=100-200

4518-10-9,Some common heterocyclic compound, 4518-10-9, name is Methyl 3-aminobenzoate, molecular formula is C8H9NO2, 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.

EXAMPLE 13-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18)SCLiOH H2O/TIH F EPO Step 1: (The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (lOlmg, 0.45mmol) and DMAP (8mg, O.Ommol) and stir for lOmin. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2- (2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J Am. Chem. Soc; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1 H, J= 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J= 7.8Hz); 7.78 (t, 1 H, J= 1.8Hz); 7.90 (dd, I H1 J/ = 8.1Hz, J2 = 1.3Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-aminobenzoate, its application will become more common.

Reference:
Patent; REVOTAR BIOPHARMACEUTICALS AG; WO2007/39112; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 42726-73-8, name is tert-Butyl methyl malonate, 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 42726-73-8, 42726-73-8

tert-Butyl methyl malonate (3.9 mL, 23 mmol), potassium carbonate (7.9 g, 57.5 mmol) and dibromoethane (2.57 mL, 29.9 mmol) were combined in DMF (75 mL) and the resulting reaction mixture was stirred at room temperature overnight. The mixture was poured onto water (500 mL) and extracted with ether (3 X). The combined ethereal layers were washed with water, then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-5percent EtOAc/ hexane) provided l-(tert-butyl) 1-methyl cyclopropane-l,l-dicarboxylate (2.35 g, 51percent yield). Combined with another batch afforded the desired product (4.28 g). 1H NMR (300 MHz, Chloroform-d) delta 3.75 (s, 3H), 1.47 (s, 9H), 1.38 (s, 4H).

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, tert-Butyl methyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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. 42726-73-8

Example 2; Preparation of Compound 2; Compound 1 (7 g), tert-butyl methyl malonate (6 g), 0.5 ml of piperidine and 0.3 ml of acetic acid are heated under reflux for three hours in 100 ml of methanol. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The concentrated filtrated is poured into water, and resulted precipitate is filtered off with suction to collect the solid that is air-dried. The crude product is further purified with silica gel chromatography to yield the desired Compound 2.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl methyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AAT Bioquest, Inc.; US8318953; (2012); B2;,
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 61644-18-6 as follows. 61644-18-6

Example 6 Isobutyroxymethyl methyl 4-(2′,3′-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate To a stirred mixture of 1,4-dihydro-2,6-dimethyl-4-(2′,3′-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (5.11 g, 14 mmol) and sodium bicarbonate (2.39 g, 28 mmol) in DMF (250 ml) under argon atmosphere was added chloromethyl isobutyrate (2.93 g, 21 mmol). The reaction mixture was heated for 80 C. for 18 h. Workup by evaporation of solvent. The crude residue was dissolved in dichloromethane and washed with sodium bicarbonate-solution. The organic layer was dried and evaporated. The residue was chromatographed on silica gel by gradient eluation (dichloromethane to 25% ethyl acetate in dichloromethane). Recrystallization from diisopropylether gave colorless crystals (3.35, 52%), mp. 145 C. 1 H-NMR (CDCl3): 7.30-7.04 (m, 3H); 5.73 (d, J=5.5 Hz, 1H); 5.71 (d, J=5.5 Hz, 1H); 5.68 (s, 1H); 5.47 (s, 1 H); 3.60 (s, 3H); 2.49 (m, 1 H); 2.33 (s, 3H); 2.31 (s, 3H); 1.10 (m, 6H). 13 C-NMR (CDCI3): 175.66; 167.62; 165.77; 147.44; 146.47; 143.78; 132.97; 131.24; 129.81; 128.33; 126.93; 103.99; 102.06; 78.89; 50.86; 38.63; 33.69; 19.83; 19.22; 18.55.

According to the analysis of related databases, 61644-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astra Aktiebolag; US5856346; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

34846-90-7, Name is Methyl 3-methoxyacrylate, 34846-90-7, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

To three reaction bottles were added 10.8 g (100 mmol) of phenylhydrazine, 11.6 g (100 mmol) of methyl methacrylate,100 mL of methanol. The temperature of the reaction mixture was raised to reflux for about 6 hours. The reaction liquid was quantified by liquid chromatography, and 1-phenyl-5-hydroxypyrazoleYield 85.7percent.

Statistics shows that Methyl 3-methoxyacrylate is playing an increasingly important role. we look forward to future research findings about 34846-90-7.

Reference:
Patent; Hunan Haili Changde Agrochemical Co.,Ltd.; Hu, Zhibin; Liu, Weidong; Du, Shenghua; Huang, Chaoqun; Lan, Shilin; Xiong, Lili; Wu, Yinyin; Cheng, Chao; Wang, Yanli; (6 pag.)CN104059020; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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. 816-27-3

(3) A mixture of ethyl 2-imino-2-ethoxyacetate (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180 ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonylformamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g).

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, 816-27-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4390534; (1983); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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. 35180-01-9.

2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carbo xylic acid (prepared by the method disclosed in) was reacted with trityl chloride to obtain 2-butyl-4-chcloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazol e-5-carboxylic acid. To a 100 ml of one-necked flask, 0,523 g of 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazol e-5-carboxylic acid, 0 124 g of potassium carbonate, and 5 ml of N,N-dimethylacetamide were added in turn The solution was stirred at the room temperature for 20 minutes. Then 0.562 g of 1-chloromethyl isopropyl carbonate was added and the mixture was reacted at 45 – 50 C for 16 h. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.724 g of oil, which was directly used in the next reaction without purification

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP2103610; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

5616-81-9, The chemical industry reduces the impact on the environment during synthesis 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, I believe this compound will play a more active role in future production and life.

To a solution of methyl-4-formyl benzoate (2.0 g, 12.2 mmol) and sarcosine /er/-butyl ester (2.7 g, 14.6 mmol) in 1 ,2-dichloroethane (60 mL) was added 10 drops of glacial acetic acid followed by sodium triacetoxy borohydride (5.6 g, 26.8 mmol). The reaction mixture was heated to 60C and stirred at this temperature for 20 hours. The solution was poured into aqueous saturated NaHCO3 and extracted twice with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to afford 1.32 g of the desired product that was used without further purification: 1H NMR (400 MHz, cfe-DMSO) delta 7.91 (d, J= 8.0 Hz, 2H), 7.44 (d, J= 8.0 Hz, 2H), 3.83 (s, 3H), 3.69 (s, 2H), 3.18 (s, 2H), 2.23 (s, 3H), 1.42 (s, 9H); ESI+ MS: m/z (rel intensity) 294 (40, M+H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-(methylamino)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; METASTATIX, INC.; WO2008/109154; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2435-36-1, These common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, 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.

Preparation of Bicyclic Amine Intermediate 3 (BAI-3) dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylateFreshly prepared lithium diisopropylamide (15 mL of n-butyllithium (2.5 M solution in hexane) and 5 mL of diisopropylamine were mixed at -30 C. in 50 mL of tetrahydrofuran) was cooled to -78 C. under nitrogen and stirred for 30 minutes. To a solution of dimethyl cyclopentane-1,3-dicarboxylate (2.67 g, 14.37 mmol) in tetrahydrofuran (12 mL) was drop added above freshly lithium diisopropylamide solution over 10 minutes (-75 C.-70 C.). The cold bath was then removed and the mixture was allowed to warm to 0 C. and maintained at that temperature for 20 minutes before being cooled to -80 C. A solution of 1-bromo-2-chloroethane (2 mL, 24 mmol) in tetrahydrofuran (25 mL) was added slowly to the reaction mixture over 35 minutes (-75 C.-70 C.). The reaction solution was then allowed to stir overnight with gradual warming to room temperature. The reaction was quenched by addition of saturated NH4Cl solution (20 mL). After removal of the solvent, 200 mL of ethyl acetate was added. The organic phase was washed with 2 N HCl (120 mL¡Á2), washed with brine and then dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/petroleum ether=1/10) to afford the titled compound. 1H NMR (400 MHz, CDCl3), delta (ppm): 3.68 (s, 6H), 2.022.03 (m, 4H), 1.91 (s, 2H), 1.68 (s, 4H); LCMS (ESI+) m/z 213.1 (M+H)+.

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 2435-36-1.

Reference:
Patent; ABBOTT LABORATORIES; US2010/267738; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2318-25-4 name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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. 2318-25-4

(1-Ethoxyformimidoyl) 1-acetic acid ethyl ester hydrochloride (50g, 0.26mol) was suspended in an ammonia-ethanol solution (300mL; prepared by saturating ethanol with ammonia gas at room temperature), which was then stirred at room temperature for 4 hours. After the reaction was completed, the precipitated salt was removed by filtration, and the filtrate was concentrated in vacuo at room temperature to reach 1/3 of the amount. Hydrochloric acid-methanol (130mL; hydrochloric acid content:7.5percent) was added to this filtrate, the solution was then concentrated under a reduced pressure to obtain 3,3-diamino-acrylic acid ethyl ester hydrochloride (40g, 0.24mol, 92percent) as a solid. The resulting 3,3-diamino-acrylic acid ethyl ester hydrochloride (2.2g, 13.2mmol) was suspended in tetrahydrofuran (40mL), triethylamine (2mL, 14.3mmol) and acrylonitrile (1.2mL, 19.3mmol) were added thereto, and the solution was refluxed for 6 hours. After the reaction was completed, the resulting triethylamine hydrochloride was filtered, and the filtrate was concentrated to obtain the title compound (0.6g, 3.3mmol, 25percent). 1H-NMR Spectrum (CDCl3) delta(ppm) :1.26 (3H, t, J=7.2Hz), 2.42-2.49 (2H, m), 2.50-2.57 (2H, m), 4.12 (2H, q, J=7.2Hz), 4.22 (2H, brs), 6.45 (2H, brs).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-ethoxy-3-iminopropionate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics