Tag: M.W=200-300

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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

General procedure: . Following GP1, under N2 atmosphere, to a 0C. solution of tert-butyl (1R,3r,5S)-3-hydroxybicyclo[3.2.1]octane-8-carboxylate (0.15 g, 1 eq., 0.66 mmol), phenol (0.07 g, 1.2 eq., 0.79 mmol), and PPh3 (0.21 mg, 1.5 eq., 0.99 mmol) in dry THF (5 mL) was added dropwise diisopropyl azodicarboxylate (0.2 mL, 1.2 eq., 0.79 mmol). The reaction crude was allowed to warm to room temperature and stirred for 16 h. Then, the mixture was quenched with HCl (10 mL) and extracted with EtOAc (25 mL). The organic extracts were washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 40%). UPLC-MS (method A): Rt. 1.86 min (TIC); ionization ES+304 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 7.30-7.23 (m, 2H), 7.01-6.95 (m, 2H), 6.92 (td, J=7.3, 1.1Hz, 1H), 4.85-4.74 (m, 1H), 4.19-4.10 (m, 2H), 2.15-2.03 (m, 2H), 1.95-1.73 (m, 4H), 1.58-1.46 (m, 2H), 1.42 (s, 9H), 1.40-1.37 (m, 1H).

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; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); A1;,
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Electric Literature of 94838-59-2, 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. 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 31: Add 30 (1.0 mmol) drop-wise to a solution of 29 (1.0 mmol) and NEt3 (2.0 mmol) in THF 10.0 mL under nitrogen at 0 C. When the reaction is completed, dilute with ethyl acetate. Wash with 1.0 M HCl, aqueous sat. NaHCO3, and brine. Dry with Na2SO4, concentrate, and purify by flash column chromatography to obtain 31.

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 4-aminophenethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
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Synthetic Route of 24036-52-0, These common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, 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.

Step A; A degassed suspension of commercially available 6-Bromo-4H- benzo[l,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80 C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2ZMeOH (1:1), filtered through an silica pad and concentrated to yield a yellow solid (5.68 ^ 89 0ZoJ MH+ = ITS).

Statistics shows that 6-Bromo-2H-1,4-benzoxazin-3(4H)-one is playing an increasingly important role. we look forward to future research findings about 24036-52-0.

Reference:
Patent; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63669; (2008); A1;,
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Synthetic Route of 3823-19-6, 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. 3823-19-6, name is 2-Bromo-N-(4-(trifluoromethyl)phenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Potassium tert-butoxide (65.2 mg, 0.581 mmol, 1.05 eq) wasadded to a solution of thiols 10a~ b (0.554 mmol, 1.00 eq) in 5mLanhydrous N,N-dimethylformamide. The mixture was stirred atroom temperature before the a-bromoacetamide (0.554 mmol,1.00eq) was added, then the mixture was stirred for another 2 h. Toafford desired thioethers 11a~ e and 11h ~ l, the resulting mixturewas diluted with 50 mL ethyl acetate, washed with water(50 mL 3), dried with anhydrous sodium sulfate, and concentratedin vacuum. The residue was purified with a silica gel chromatographycolumn as white or pale yellow solid of 41e63% yield.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N-(4-(trifluoromethyl)phenyl)acetamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Han, Sheng; Sang, Yali; Wu, Yan; Tao, Yuan; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen, Fen-Er; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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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. 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of Benzyl (2,2-dimethoxyethyl)carbamate

To a solution of benzyl N-(2,2-dimethoxyethyl)carbamate (1700 g, 7.10 mol), KOH (1755 g, 31.28 mol) and benzyltriethylammonium chloride (32.37g, 142.1 mmol) in toluene (7.82 L) was added 3-bromoprop-1-ene (1117.4 g, 9.24 mol) dropwise with stirring at room temperature. The resulting solution was stirred for 24 h at room temperature. Two batches were thus run in parallel. The reaction was then quenched by the addition of 10 L of water. The resulting solution was extracted with 2×7 L of toluene and the organic layers combined. The organic phase was washed with 2×10 L of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to afford benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en- 1 -yl)carbamate as 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; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
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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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (tert-butoxycarbonyl)oxycarbamate

Example 17: 7¾ -butyl i2-fl2-amino-3-chloro-6,7,10,ll-tetrahydro-7,ll- methano cvcloocta[bl uinolin-9-yl)ethyll (tert- butox carbonvDoxyl carbamate (HUP 16)A solution of tert-butyl-N-(tert-butoxycarbonyl)-carbamate (140 mg, 0.6 mmol) in anhydrous DMF (1.3 mL) was treated with sodium hydride (60% in oil, 26 mg, 0.65 mmol). The reaction mixture was stirred 40 min at r.t. and treated with a solution of mesylate (HUP 13) (157 mg, 0.4 mmol) in anhydrous DMF (2 mL). The reaction mixture was stirred at r.t. for 120 h, then at 60 C for 5 h. The mixture was then diluted with water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic layers were washed with brine (50 mL), then water (50 mL), dried with Na2S04 and concentrated under reduced pressure to afford a yellow solid (313 mg). Purification by flash chromatography (AcOEt / MeOH 10/0 to 8/2, v/v) afforded the desired Huprine (HUP 16) as a white solid (98 mg, 46%).Rf (AcOEt / MeOH 8/2, v/v) = 0.50.m.p. = 114C (decomposition).1H NMR (300 MHz, CDC13): delta = 1.41 (s, 9H, N-Boc or O-Boc), 1.46 (s, 9H, N- Boc or O-Boc), 1.84-2.02 (m, 3H, Hio, ¾), 2.10-2.22 (m, 2H, Hi4), 2.52 (dd, J = 17.1 Hz, J = 3.4 Hz, 1H, ¾), 2.67-2.71 (m, 1H, H7), 2.89 (d, J = 17.5 Hz, 1H, H6), 3.06 (dd, J = 17.6 Hz, J = 5.6 Hz, 1H, H6), 3.14-3.18 (m, 1H, Hn), 3.66-3.88 (m, 2H, His), 5.03 (brs, 2H, NH2), 5.56 (d, J = 5.1 Hz, 1H, H8), 7.21 (dd, J = 9.0 Hz, J= 1.9 Hz, 1H, H2), 7.67 (d, J= 9.0 Hz, 1H, ¾), 7.77 (d, J= 1.9 Hz, 1H, H4). 13C NMR (75 MHz, CDC13): delta = 27.4 (Cn), 27.6 (N-Boc or O-Boc), 28.1 (N-Boc or O-Boc), 28.2 (C7), 28.9 (C10), 33.8 (C13), 34.8 (Ci4), 39.4 (C6), 68.1 (Ci5), 82.3 (C-Me3 of N-Boc), 84.9 (C-Me3 of O-Boc), 115.1 (Cna or Ci2a), 115.8 (Cna or Ciza), 122.0 (Ci), 124.6 (C2), 126.9 (C4), 127.0 (C8), 132.9 (C3), 134.6 (C9), 146.5 (C4a or Ci2), 147.0 (C4a or C12), 152.2 (C=0 of N-Boc), 154.8 (C=0 of O-Boc), 158.3 (C5a).MS (ESI+): m/z (%): 530.20 (100) [M+H]+, 532.20 (39).ICso rh-AC E : 14.8 +/- 3.2 nM.ICso r/i-BuChE : 421 +/- 72 nM.

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; UNIVERSITE DE ROUEN; RONCO, Cyril; RENARD, Pierre Yves; JEAN, Ludovic; NACHON, Florian; ROMIEU, Anthony; WO2011/124712; (2011); A1;,
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Electric Literature of 201162-53-0,Some common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, molecular formula is C11H20N2O2, 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.

3,8-diazabicyclo [3.2.1] octane-3-carboxylic acid tert-butyl ester (320 mg, 1.5 mmol)And bromoethane (817 mg, 7.5 mmol)Was dissolved in acetonitrile (50 mL), potassium carbonate (1.03 mg, 7.5 mmol) was added and reacted at 40 C for 16 hours.The organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound which was extracted with ethyl acetate (50 mL) The title compound was obtained as a color oil (350 mg, yield 97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Boc-3,8-Diazabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
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Synthetic Route of 94838-59-2, 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 94838-59-2 as follows.

A mixture of 2-(3-bromopropoxy)tetrahydro-2//-pyran (669mg,3 mmol), tert- butyl 4- aminophenethylcarbamate (709 mg, 3 mmol) and cesium carbonate (2.9 g, 9 mmol) in DMF (20 mL) was stirred at 110 C for 2 h. TLC showed the reaction completed. The reaction mixture was filtered. The filtrate was concentrated and purified by column chromatography to afford the title compound as yellow oil (l80mg, 15.9% yield). NMR (500 MHz, DMSO-r/6) S: 6.94 (d, J= 8.3 Hz, 2H), 6.84 (t, J= 5.4 Hz, 1H), 6.54 (d, J= 8.4 Hz, 2H), 5.42 (t, J= 5.6 Hz, 1H), 4.61 (t, J= 3.4 Hz, 1H), 3.79 (tt, J= 12.6, 4.8 Hz, 2H), 3.49 (dt, J= 9.4, 6.2 Hz, 2H), 3.16 – 3.02 (m, 4H), 2.58 (d, J= 8.0 Hz, 2H), 1.87 – 1.64 (m, 4H), 1.57 – 1.47 (m, 4H), 1.41 (d, J= 15.5 Hz, 9H).

According to the analysis of related databases, 94838-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
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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;,
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Related Products of 123986-64-1, 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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(4-Hydroxymethyl~benzyl)-carbamic acid tert-butyl ester (480 mg, 0.71 mmol) was dissolved in DCM (3 ml_) and cooled to -78 0C (dry ice / acetone). Dess-Martin periodinane (331 mg, 0.78 mmol) was added to the reaction which was allowed to warm to r.t and stir for 3 h. A 1 :1 solution of saturated sodium bicarbonate and sodium sulfite (20 ml_) was added and the reaction mixture stirred vigorously for 15 min. The organic layer was isolated, washed with saturated sodium bicarbonate (10 ml_), dried (Na2SO4) and evaporated to dryness to afford the desired compound (480 mg, 100%). m/z 258 [M++Na]+

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 4-(hydroxymethyl)benzylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/117549; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics