Month: June 2021

Related Products of 55666-42-7, 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. 55666-42-7, name is tert-Butyl 2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

tert-Butyl 2-bromobenzoate (129 mg, 0.502 mmol) and anhydrous THF (5 mL) were put into a dried flask inside of which was substituted with argon. The mixture was cooled to -78 C., and then added with 1M sec-BuLi (0.30 mmol), and the mixture was stirred for 20 minutes. The mixture was slowly added with 4,5-dichloro-3,6-diOTBDMS-Si-xanthone (11.3 mg, 0.0200 mmol) dissolved in anhydrous THF (5 mL) at the same temperature, and the mixture was returned to room temperature. The mixture was stirred at room temperature for 1 hour, and then added with 2 N HCl (10 mL), and the mixture was stirred for 20 minutes. The mixture was extracted with dichloromethane, and the organic layer was washed with brine, and dried over Na2SO4. The solvent was removed, then the residue was added with TFA (5 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was removed, and then the residue was purified by HPLC to obtain 2-COOH DCTM (5.7 mg, 0.013 mmol, yield 64%). 1H-NMR (400 MHz, CD3OD): delta 0.83 (s, 3H), 0.98 (s, 3H), 6.85 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 6.98 (d, 1H J=7.8 Hz), 7.51 (td, 1H, J=1.0, 7.6 Hz), 7.60 (td, 1H, J=1.0, 7.6 Hz), 7.90 (d, 1H, J=7.8 Hz) 13C-NMR (100 MHz, CD2COCD2): delta-0.2, 0.5, 90.0, 119.8, 123.6, 124.3, 126.4, 127.1, 127.8, 129.9, 135.1, 136.2, 136.7, 153.6, 158.3, 171.2 HRMS (ESI+): m/z Found 443.0241, calculated 443.0273 for [M+H]+ (-3.2 mmu)

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

Reference:
Patent; THE UNIVERSITY OF TOKYO; Nagano, Tetsuo; Hanaoka, Kenjiro; Koide, Yuichiro; Egawa, Takahiro; Hirabayashi, Kazuhisa; US2013/289256; (2013); A1;,
Ester – Wikipedia,
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Related Products of 4224-69-5, 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 4224-69-5 as follows.

Cyclopentylamine (5.79 mL, 58.7 mmol, 3.00 eq) and triethylamine (2.73 mL, 19.6 mL, 1.00 eq) were added to DCM (98 mL) and the reaction was cooled to 0 C. Methyl 2-(bromomethyl)acrylate (2.35 mL, 19.6 mmol, 1.00 eq) in DCM (48 mL) was added dropwise. Following addition the reaction was stirred for an additional 30 minutes at 0 C. Water was added and the layers separated. The aqueous layer was extracted with an additional portion of DCM and the combined organics were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using 0- 60% DCM/MeOH/NH4OH (89: 10: 1) afforded 1.19 g (33%) of the title compound as a clear oil: 1H MR (400 MHz, DMSO-d6) 3 6.10 (s, 1H), 5.79 (s, 1H), 3.67 (s, 3H), 3.65 (d, J= 5.9 Hz, 1H), 3.56 (d, J= 15.1 Hz, 1H), 3.21 (d, J= 7.4 Hz, 1H), 2.98 (p, J= 6.2 Hz, 1H), 1.72-1.22 (m, 8H); ES-MS [M+l]+: 184.4.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; NISWENDER, Kevin; (90 pag.)WO2017/117556; (2017); 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 36692-49-6

To a solution of trans-3′-oxospiro [cyclohexane- [1,] [1′ (3’H)-ISOBENZOFURAN]-4-CARBOXYLIC ACID] (20 mg, 0.081 mmol) and methyl 3,4-diaminobenzoate (20 mg, 0.12 mmol) in pyridine (1 mL) was added 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol). The mixture was stirred at room temperature for one hour under a nitrogen atmosphere, and then concentrated. After addition of saturated aqueous sodium bicarbonate to the residue, the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was washed with ethyl acetate-hexane, and dried to give the title compound (30.4 mg, 95 [%).]

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; WO2004/2986; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2208-05-1, name is 2-(Dimethylamino)ethyl benzoate, 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 2208-05-1, COA of Formula: C11H15NO2

EXAMPLE 39 N,N-Bis(2-(Benzoyloxy)ethyl)-N,N-dimethylammonium bromide Equimolar amounts of 2-bromoethyl benzoate (45.8 g) and 2-(N,N-dimethylamino)ethyl benzoate (38.5 g) were dissolved in 170 ml of acetonitrile and heated at reflux for 16 hours. The reaction mixture was then cooled and the resultant solid was collected, washed with ether, and dried to yield 62.4 g of the title compound, mp=169°-70° C. Anal. Calcd. for C20 H24 BrNO4: C, 56.88; H, 5.73; N, 3.32; Found: C, 56.49; H, 5.68; N, 3.38.

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, 2-(Dimethylamino)ethyl benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eastman Kodak Company; US5194472; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, molecular formula is C10H13NO2, 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: C10H13NO2

tert-Butyl 4-(3-(2-ethoxy-2-oxoethyl)-3-phenylureido)piperidine-1-carboxylate. 4-Amino-1-N-Boc-piperidine (760 mg, 3.79 mmol) was dissolved in a mixture of dichloromethane (40 mL) and aqueous sodium bicarbonate (30 mL). A solution of 20% phosgene in toluene (10 mL, 18.9 mmol) was added to the mixture with vigorous stirring. Reaction stirred vigorously at room temperature for 40 minutes. Reaction layers were partitioned. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was dissolved in toluene (30 mL). N-Phenylglycine ethyl ester was added to the mixture. Reaction was heated at reflux for 15 hours. Mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). Mixture was washed successively with 1N hydrochloric acid (3×50 mL) and brine (30 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as pale yellow solid in 63% yield. 1H NMR (300 MHz, CDCl3): delta=7.47-7.26 (m, 5H), 4.30 (s, 1H), 4.16 (q, J=7.32, 2H), 3.88 (d, J=12.81, 2H), 3.81-3.69 (m, 1H), 2.89-2.70 (m, 2H), 1.83 (dd, J1=12.62, J2=3.11, 2H), 1.38 (s, 9H), 1.23 (t, J=7.14, 3H), 1.19-1.03 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2216-92-4, its application will become more common.

Reference:
Patent; Chaturvedula, Prasad V.; Mercer, Stephen E.; Fang, Haiquan; US2006/94707; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 179022-43-6, 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 179022-43-6 as follows.

Example 27: 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen-2-yl) azabicyclo[3.2.1]octane-3-carboxylic acid To a solution of methanesulfonic acid 5-(4-methyl-cyclohexyloxy)-naphthalen-2- ylmethyl ester (177 mg, 0.508 mmol) in DMF (2 mL), 8-aza-bicyclo[3.2.1]octane-3- carboxylic acid methyl ester HCl salt (208.38 mg, 1.0131 mmol) was added, followed by cesium carbonate (495.14 mg, 1.5197 mmol). The reaction was then heated at 80 C for lh. After cooled down, the reaction mixture was diluted with EtOAc, washed with water (2x). The organic phase was then separated, dried and concentrated. The crude was purified by HPLC, removed the solvent, the ester was then dissolved in tetrahydrofuran (2.3 mL, 29 mmol) , treated with 1.0 M of lithium hydroxide in Water(3.5 mL, 3.5 mmol) at rt overnight. Acidified with 1NHC1, the organic layer was dried and concentrated. The crude was then purified by HLPC to give 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen- 2-yl)methyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid as a white powder (132.9 mg, 64% ). LCMS: RT 1.40 min.; MH+ 408.1. 1H NMR (400 MHz, METHANOL-d4) delta 8.38 (d, J = 8.72 Hz, 1H), 7.98 (s, 1H), 7.60 (d, J = 10.48 Hz, 1H), 7.46 (d, J = 4.96 Hz, 2H), 6.92 – 7.08 (m, 1H), 4.85 (br. s., 1H), 3.80 – 4.45 (m, 2H), 3.37 (s, 2H), 1.35 -2.81 (m, 18H), 1.00 (d, J = 5.65 Hz, 3H).

According to the analysis of related databases, 179022-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; SUN, Lihong; XIN, Zhili; ZHANG, Lei; WO2014/25708; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 623-47-2,Some common heterocyclic compound, 623-47-2, name is Ethyl propiolate, molecular formula is C5H6O2, 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 ethyl propionate (A-3) (26.3 g, 0.268 mol) and AgNCb (4.56 g, 26.8 mmol) in anhydrous acetone (300 mL) was added NBS (52.6 g, 0.295 mol) in several small portions at 0 C and stirred at room temperature overnight. The mixture was filtered. The filtrate was diluted with H2O (500 mL) and extracted with n-hexane (500 mL x 3). The combined extracts were washed with an aqueous HC1 solution (10%, 500 mL x 2) and brine (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure at room temperature (ESI) m/z: non- ionizable compound under routine conditions used; -NMK (CDCb, 400 MHz): d (ppm) 1.32 (t, J= 7.2 Hz, 3H), 4.25 (q, J= 7.2 Hz, 2H).

The synthetic route of 623-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-71-4,Some common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

2-Methyl-benzoic acid methyl ester (1.50 g 10 mmol), N-bromo-succinimide (1.96 g, 11 mmol) and 2,2′-azobis(2-methyl-propionitrile) (AIBN) (25 mg, 0.15 mmol) were dissolved in chloroform (3 ml). The solution was heated at reflux for 16 hours cooled and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (1-2 %) as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 2.05 g (89 %) of 2-bromomethyl-benzoic acid methyl ester as a solid. 1H-NMR (CDCl3): delta 7.97 (d, 1H, J = 7.6 Hz), 7.45-7.52 (m, 2H), 7.38 (dt, 1H, J = 1.2 Hz and J = 7.6 Hz), 4.96 (s, 2H), 3.95 (s, 1H). To a solution of 2-amino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (100 mg, 0.20 mmol) and pyridine (0.18 ml, 2.0 mmol) in acetonitrile (1 ml) at room temperature was added benzyl chloroformate (0.28 ml, 2.0 mmol) in 10 aliquots over 48 hours. The solution was then taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate (3 x 10 ml), brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The resulting oil crystallized upon standing for 2 days. The precipitate was filtered off and washed with diethyl ether (3 x 1 ml) affording after drying in vacuo 59 mg (47 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.60 (s, 1H), 7.60-7.92 (m, 4H), 7.38 (m, 5H), 5.26 (s, 2H), 4.30-5.10 (m, 3H), 3.40-4.00 (m, 2H), 1.57 (m, 9H), 1.15 (m, 9H). To a solution of 1 N hydrochloric acid in ethyl acetate (1.0 ml) was added 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (52 mg, 0.08 mmol). The solution was stirred at room temperature for 48 hours. A precipitate was filtered off which afforded 42 mg (90 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride as a solid. 1H-NMR (DMSO-d6): delta 10.45 (s, 1H), 9.40 (s, 1H), 9.25 (s, 1H), 7.89 (m, 4H), 7.39 (m, 5H), 5.22 (s, 2H), 4.39 (d, 1H, J = 15 Hz), 4.28 (m, 1H), 3.95 (m, 2H), 3.79 (m, 1H), 3.20 (m, 1H), 2.70 (m, 1H), 1.48 (s, 9H). To a solution of the above 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride (42 mg, 0.072 mmol) in ethanol (0.5 ml) was added hydrazine (68 mul, 0.22 mmol). The solution was stirred at 80 C for 5 hours and at room temperature for 16 hours. The mixture was filtered and the filtrate evaporated in vacuo. The residue was extracted with dichloromethane (5 x 1 ml). The combined dichloromethane washes were evaporated in vacuo affording 20 mg (67 %) of 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil. 1H-NMR (CDCl3): delta 10.55 (bs, 1H), 7.37 (m, 5H), 5.23 (s, 2H), 3.92 (s, 2H), 2.60-3.10 (m, 3H), 1.53 (s, 9H). To a solution of the above 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.048 mmol) in acetonitrile (1 ml) at 0 C was added diisopropylethylamine (18 l, 0.15 mmol) and 2-bromomethyl-benzoic acid methyl (12 mg, 0.048 mmol). The solution was stirred at 0 C for 3 hours and at room temperature for 16 hours. Di-tert-butyl dicarbonate (21 mg, 0.096 mmol) was then added to the solution. The solution was then stirred at room temperature for 16 hours. The solution was taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3 x 10 ml), saturated sodium bicarbonate (3 x 10 ml) and brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The solid residue was purified by silica gel chromatography using a 5 % mixture of ethyl acetate/hexane as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 10 mg (33 %) of 2-(benzyloxycarbonylamino)-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.59 (s, 1H), 7.81 (m, 1H), 7.52 (m, 1H), 7.39 (m, 7H), 5.25 (s, 1H), 4.22-5.00 (m, 4H), 4.40-4.80 (m, 2H), 2.80-3.10 (m, 2H), 1.55 (s, 9H), 1.25 (s, 9H). To a solution of the above 2-benzytoxycarbonylamino-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (9 mg, 0.014 mmol) in methanol (2 ml) was added 10 % Pd/C (4 mg). The mixture was stirred under hydrogen (1 atm.) for 3 hours and then filtered. The filtrate was evaporated in vacuo affordi…

The synthetic route of 89-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214324; (2006); B1;,
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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H10N2O2

Example 5 Synthesis of methyl 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-carboxylate A solution of methyl-1,2-phenylenediamine-4-benzoate (0.1 mol) and isatoic anhydride (0.1 mol) in acetic acid (75%) was heated at 120 C. for 2 hrs. The mixture was diluted with water and extracted with dichloromethane, washed with water and dried over Na2SO4. Methyl 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-carboxylate was isolated (92%) after removal of solvent under reduced pressure.

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; US2010/228023; (2010); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H13BrO4

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics