Category: 53844-02-3

Application of 53844-02-3, A common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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 bromide (1 mmol) and 4-amino-1-butanol (0.36 g, 4 mmol, 4 eq.) in anhydrous DMF (10 ml) under N2, was added anhydrous K2CO3 (0.276 g, 2 mmol, 2 eq.) and sodium iodide (15 mg, 0.1 mmol, 0.1 eq.). The reaction was stirred for 72 hours at room temperature, until reaction complete. The DMF was evaporated in vacuo and dried exhaustively under high vacuum. The resulting oily solid was redissolved in CH2Cl2 (100 ml) and washed with water (4 x 50 ml). The combined aqueous extracts were then washed with CH2Cl2 (40 ml) and the CH2Cl2 extracts dried over anhydrous Na2SO4. The CH2Cl2 was evaporated in vacuo to give a pale yellow oil.

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; IC-VEC LIMITED; EP918790; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53844-02-3,Some common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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.

Treat a -78 C solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, drop-wise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to -30 C for 0.5 h, re-cool to -78C and treat drop-wise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at -78C for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at – 78C for 1 h, then warm to RT and stir overnight. Treat the mixture with H20, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2S04, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21 % yield). MS (m/z): 247.2 (M+l).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; ELI LILLY AND COMPANY; FLYNN, Daniel L.; KAUFMAN, Michael D.; VOGETI, Lakshminarayana; WISE, Scott C.; LU, Wei-Ping; SMITH, Bryan D.; CALDWELL, Timothy M.; PATT, William C.; HENRY, James Robert; HIPSKIND, Philip Arthur; PENG, Sheng-Bin; WO2013/134298; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (60%, 120mg, 3.0mmol) was added to a solution of 2-tert-butoxycarbonylamino-3-fluorobenzoic acid methyl ester from Example 20A (750mg, 2.8mmol) in DMF (8.0ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 30min. (2-bromoethyl)carbamic acid benzyl ester (360mg, 2.8mmol) and sodium iodide (420mg, 2.8mmol) were added and the mixture was heated at 65C for 18h. The mixture was cooled and evaporated in vacuo. The residue was partitioned between EtOAc and brine and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (EtOAc:pet. ether 30:70) to give a colourless gum; yield 340mg, 27%.

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

Reference:
Patent; FERRING B.V.; WO2006/18443; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of benzyl(2-bromoethyl)carbamate 9 (129 mg, 0.5 mmol) and the corresponding Michael acceptor 11 (0.5 mmol) in THF (2.5 mL) at 0 C, was added NaH (60% in mineral oil, 24 mg, 0.6 mmol) portion by portion. The ice bath was removed and the reaction mixture was stirred for 3 h to 3 days (monitored by TLC), was then poured into a saturated NH4Cl solution, and extracted with ethyl acetate (2 25 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography (cyclohexane/EtOAc: 20/ 80).

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Goermen, Meral; Le Goff, Ronan; Lawson, Ata Martin; Daich, Adam; Comesse, Sebastien; Tetrahedron Letters; vol. 54; 17; (2013); p. 2174 – 2176;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, belongs to amides-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 53844-02-3, HPLC of Formula: C10H12BrNO2

1.7 g of 5-hydroxy-2-nitrophenyl ethanol and 4.3 g of potassium carbonate were dispersed in 20 ml N, N’- dimethyl formamide, and heated to 60 deg.] C for 1 hour. It was slowly added dropwise 2.82 g N- benzyloxycarbonyl-BrEA in methylene chloride (5 ml), 60 reaction for 24 hours. After completion of the reaction, the solvent was removed under reduced pressure, the product was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution, and saturated sodium chloride solution each, washed twice with distilled water wash, the organic phase was dried over anhydrous magnesium sulfate and 8 hours, filtered after concentration under reduced pressure, ethyl acetate / cyclohexane recrystallized twice to give product A.Take 1.56 g of product A was dissolved in 50 ml of anhydrous dichloromethane, was added under ice-cooling 1.25 g N- benzyloxycarbonyl-methionine, 1.33 g N, N’- dicyclohexyl carbodiimide and 0.2 g 4 – dimethylaminopyridine, stirred at room temperature overnight. After completion of the reaction, diluted hydrochloric acid with ice, saturated sodium bicarbonate solution and saturated sodium chloride solution each, washed twice with distilled water wash, dried over anhydrous sodium sulfate overnight. Suction filtered and the solvent was removed under reduced pressure, recrystallized twice from ethyl acetate. The obtained crystals were dissolved in 20 ml of chloroform, 20 ml of hydrogen chloride in ethyl acetate under ice-cooling a saturated solution, after 6 hours at room temperature the reaction dried under reduced pressure to give the productB. The product B was dissolved 0.687 g of methylene chloride and 50 ml of a mixed solvent of 8 ml of pyridine, cooled to -18 deg.] C, was added dropwise 10 ml of a toluene solution of phosgene (1.93 mol per liter) for 6 hours. The reaction mixture was washed with dilute hydrochloric acid each and twice with saturated sodium bicarbonate solution, saturated sodium chloride solution and distilled water for each wash. The organic phase was dried overnight over anhydrous magnesium sulfate, concentrated under reduced pressure after filtration

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (2-bromoethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan University; Ding, Mingming; Wang, Rui; Wu, Qiang; Tan, Hong; Zhang, Qin; Li, Jiehua; (14 pag.)CN105601550; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 53844-02-3, A common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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 bromide (1 mmol) and 4-amino-1-butanol (0.36 g, 4 mmol, 4 eq.) in anhydrous DMF (10 ml) under N2, was added anhydrous K2CO3 (0.276 g, 2 mmol, 2 eq.) and sodium iodide (15 mg, 0.1 mmol, 0.1 eq.). The reaction was stirred for 72 hours at room temperature, until reaction complete. The DMF was evaporated in vacuo and dried exhaustively under high vacuum. The resulting oily solid was redissolved in CH2Cl2 (100 ml) and washed with water (4 x 50 ml). The combined aqueous extracts were then washed with CH2Cl2 (40 ml) and the CH2Cl2 extracts dried over anhydrous Na2SO4. The CH2Cl2 was evaporated in vacuo to give a pale yellow oil.

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; IC-VEC LIMITED; EP918790; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 53844-02-3,Some common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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.

Treat a -78 C solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, drop-wise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to -30 C for 0.5 h, re-cool to -78C and treat drop-wise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at -78C for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at – 78C for 1 h, then warm to RT and stir overnight. Treat the mixture with H20, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2S04, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21 % yield). MS (m/z): 247.2 (M+l).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; ELI LILLY AND COMPANY; FLYNN, Daniel L.; KAUFMAN, Michael D.; VOGETI, Lakshminarayana; WISE, Scott C.; LU, Wei-Ping; SMITH, Bryan D.; CALDWELL, Timothy M.; PATT, William C.; HENRY, James Robert; HIPSKIND, Philip Arthur; PENG, Sheng-Bin; WO2013/134298; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to the described general procedure (GP11), N-alkylation of commercially available 4(5)-methylimidazole (4.343 g ; 52.90 mmol) with (2-bromo-ethyl)-carbamic acid benzyl ester (15.019 g ; 58.19 mmol), and subsequent purification by FC (DCM /MeOH =10/1) afforded a mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester, and [2-(5-methyl-imidazol-1-yl)ethyl]-carbamic acid benzyl ester (ratio of regioisomers close to 1/1, according to 1H-NMR) as a yellow oil (4.270 g ; 31%). LC-MS: tR=0.68 min. (2 regioisomers); [M+H]+: 260.46 g/mol. A mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]carbamic acid benzyl ester, [2-(5-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester (1.198 g; 4.62 mmol; ratio of regioisomers close to 1/1, according to 1H-NMR), and 10% palladium on activated charcoal (240 mg; 20% in mass) was placed under nitrogen before addition of anh. MeOH (20 ml). The resulting mixture was placed under vacuum, and then under hydrogen (1 atm), and stirring at rt was continued for 2.5 h. Filtration over a pad of celite, concentration to dryness under reduced pressure afforded a mixture of 2-(4-methyl-imidazol-1-yl)-ethylamine, and 2-(5-methyl-imidazol-1-yl)-ethylamine as a slightly yellow oil (540 mg; 93%). LC-MS: tR=0.17 min. (2 regioisomers); [M+H]+: no ionisation. These primary amines were converted to the corresponding chlorhydrate salt by treatment of a solution of regioisomeric amines (540 mg ; 4.31 mmol) in dichloromethane (5 ml) with 4N HCl in 1,4-dioxane (3.25 ml ; 3 eq.). Concentration to dryness under reduced pressure afforded a beige solid which was further dried under HV.

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (2011); A1;,
Amide – Wikipedia,
Amide – 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 53844-02-3

The compound of Reference Example 55 (12.3 g) was dissolved in dimethylformamide (100 ml), and thereto were added cesium carbonate (15.3 g) and the compound of Reference Example 42 (8.75 g), and the mixture was vigorously stirred at 80C for 5 hours. The mixture was filtered to remove the cesium carbonate, and water was added to the filtrate, and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column (ethyl acetate/hexane=1:2) to give the title compound (10.7 g). MS (ESI+) 649 (M++1, 40%).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2447264; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1 (15.0mmol) in CH3CN (60mL) were added K2CO3 (3.10g, 22.5mmol) and N-Cbz-2-bromoethylamine (3.87g, 15.0mmol) under stirring. It was then kept at 80C, and monitored by TLC (Hexane/EtOAc=2/1, v/v). Next, K2CO3 was removed by filtration. The filtrate was concentrated to give a light brown oil. The oil was dissolved in ethyl acetate (150mL) and the solution was washed with water (2¡Á50mL). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. The residue was concentrated and purified by silica gel column chromatography (Hexane/EtOAc=4/1, v/v) to give a white solid

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ao, Chunyan; Men, Jian; Wang, Yang; Shao, Tao; Huang, Yuanyuan; Huo, Junji; Gao, Guowei; Tetrahedron Asymmetry; vol. 27; 13; (2016); p. 589 – 595;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics