Tag: M.W=200-300

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. 610302-03-9, name is tert-Butyl (3-hydroxycyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C11H21NO3

Step 1. tert-Butyl (3-((4- bromobenzyl)oxy)cyclohexyl)carbamate. To a stirring solution of tert-butyl (3- hydroxycyclohexyl)carbamate (220 mg, 1.02 mmol) in THF (3 mL) at 0 C was added NaH (41 mg, 1.02 mmol) and stirred at 0 C for 30 mins, then 4-bromobenzyl bromide (255 mg, 1.02 mmol) was added and the reaction mixture was warmed to rt and stirred for 3h. The reaction mixture was cooled to 0 C, and quenched by the dropwise addition of sat. ammonium chloride, extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography using 10 – 25% EtOAc/Hexanes gradient elution to afford tert-butyl (3-((4- bromobenzyl)oxy)cyclohexyl)carbamate as a white solid (184 mg, 48%): NMR (500MHz, CDCk) delta ppm 7.45 (d, J= 8.3 Hz, 2H), 7.21 (d, J= 2H), 4.92 (bs, 1H), 4.48 (s, 2H), 3.55 (m, 1H), 3.45 (bs, 1H), 2.19 (d, 11.72 Hz, 1H), 1.70 – 1.95 (m, 3H)1.44 (s, 9H), 1.15 – 1.37 (m, 4H).

The synthetic route of 610302-03-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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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 177906-48-8 as follows. SDS of cas: 177906-48-8

To a stirred mixture of 6-chloroquinoline-2-carboxylic acid (100 mg, 0.48 mmol, 1 equiv) and trans-tert-butyl (4-aminocyclohexyl)carbamate (103 mg, 0.48 mmol, 1 equiv) in DMF (5 mL) was added HATU (365 mg, 0.96 mmol, 2 equiv) and continued stir at RT for 30 min. DIPEA (0.3 ml, 1.44 mmol, 3 equiv) was added and again stirred at RT for overnight. Reaction progress was monitored by LCMS. After completion of reaction, the reaction mixture was poured into water (50 mL), the resulting yellow precipitate was filtered off and again washed with water (20 mL×2). Thus obtained solid was dried under vacuum to obtain trans-tert-butyl (4-(6-chloroquinoline-2-carboxamido)cyclohexyl)carbamate (120 mg, 71.85%) as a yellow solid. LCMS: 404.6 [M+H]+

According to the analysis of related databases, 177906-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Praxis Biotech LLC; BERNALES, Sebastian; DELGADO OYARZO, Luz Marina; NUNEZ VASQUEZ, Gonzalo Esteban; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; CHAKRAVARTY, Sarvajit; US2019/177310; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1232365-42-2, name is tert-Butyl (3,3-difluoro-1-(hydroxymethyl)cyclobutyl)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 1232365-42-2, SDS of cas: 1232365-42-2

Tert-Butyl N- [3,3 -difluoro- 1 -(hydroxymethyl)cyclobutyl] carbamate (900 mg, 3.79mmol) was dissolved in 25 mL of 4M HC1/dioxane at r.t. and the resulting mixture was stirredovernight. Upon completion of the reaction (monitored by 1 H NMR), the resulting mixture was concentrated under reduced pressure, the residue was treated with 20 mL of acetonitrile, and filtered. The precipitate was washed with acetonitrile and dried in vacuo to obtain (1-amino-3,3- difluorocyclobutyl)methanol hydrochloride (550.0 mg, 3.17 mmol, 83.5% yield) as whitepowder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3,3-difluoro-1-(hydroxymethyl)cyclobutyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; AICURIS GMBH & CO. KG; DONALD, Alastair; URBAN, Andreas; BONSMANN, Susanne; WEGERT, Anita; GREMMEN, Christiaan; SPRINGER, Jasper; (376 pag.)WO2019/86141; (2019); A1;,
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Application of 120157-96-2, 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. 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To a solution of the compound obtained in the above step (1) (1.5 g) in tetrahydrofuran (15 mL) was added 60 % oily dispersion of sodium hydride (407 mg) under ice-cooling and the mixture was stirred at room temperature for 30 minutes. Thereto was added dropwise ethyl iodide (2.26 mL) under ice-cooling and the mixture was stirred at 60 C for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (10 mL) and thereto was added water (20 mL). After stirring, the organic layer was separated and concentrated and the resultant residue was purified by a flash column chromatography on NH-silica gel (Solvent; n-hexane/ethyl acetate = 20: 1) to give methyl 4-[[N-ethyl-N-(tert-butoxycarbonyl)]aminomethyl]benzoate (929 mg, yield: 56 %) as an amorphous solid. MS(APCI)m/z; 294 [M+H]+

The synthetic route of Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1772454; (2007); A1;,
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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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(Trifluoromethyl)thiobenzamide

4- (Trifluoromethyl) thiobenzamide (20.5 g, 0.1 mol) was dissolved in tetrahydrofuran (300 [UN)] at room temperature, and then methyl [2-CHLOROACETOACETATE] (12.2 [UN,] 0.1 mol) was added slowly for about 20 minutes therein while stirring. After completion of addition, the mixture was stirred again at room temperature for 30 minutes, and then the mixture was heated and refluxed at 78 to 80 C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, 50% aqueous solution of sodium hydroxide [(150 NE)] was added and stirred for 20 minutes. The resultant organic layer was separated by extraction with ethyl acetate, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to thereby yield 28.8 g of the title compound (yield: 95. 6%). ‘H-NMR (300 MHz, [CDCI3)] : 8.01 (d, 2H, [J =] 8.4 Hz), 7.64 (d, 2H, [J= 8. 3] Hz), 3. 84 [(S, 3H),] 2. [73] (s, [3H).]

According to the analysis of related databases, 72505-21-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANG, Heonjoong; HAM, Jungyeob; WO2003/106442; (2003); A1;,
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Synthetic Route of 118753-70-1,Some common heterocyclic compound, 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, molecular formula is C9H17Cl2NO2, 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.

A solution containing bis(2-chloroethyl)-N-BOC amine (described in US Patent 5,661, 163) (8.15 g, 33.67 mmol), 3,4-dichlorophenylacetonitrile (5.05 g, 27.17 mmol), and DMSO (50 mL) was stirred at RT and solid cesium carbonate (17.6 g, 54.02 mmol) was added (in portions) over 10 minutes. After 20 h, additional cesium carbonate (1.7 g, ) was added, and the mixture stirred for an additional 72 h. The mixture was partitioned between water and EtOAc, the aq. layer was removed, and the organic layer washed successively with additional water,0.1M aq. HCl (2X), sat. aq.NaHC03, and brine. The organic layer was dried, filtered, concentrated, and the residue triturated (3: 1 hexane/ethyl acetate) to give the title compound as an off-white solid, m. p.142-145 C. MS m/z 255. 1H NMR (CDC13) 6 7.55 (d,1H), 7.49 (d, 1H), 7.32(m,1H), 4.3 (br d, 2H), 3.18 (br t, 2H), 2.07 (d, 2H), 1.89(m, 2H), 1.48 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl bis(2-chloroethyl)carbamate, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2004/20411; (2004); A1;,
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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. 71026-66-9, name is tert-Butyl (4-aminophenyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (4-aminophenyl)carbamate

2,4-dichloro-5-nitropyrimidine (190 mg, 0.98 mmol) 6 mL of 1,4-dioxane was added,Placed in a 25 mL round bottom flask, Stirred at room temperature,(4-aminophenyl)Tert-butyl carbamate(200 mg, 0.96 mmol),N,N-diisopropylethylamine (137 mg, 1.06 mmol)Dissolved in 4 mL of 1,4-dioxane, Slowly added dropwise to the above reaction solution,After the addition was continued, the mixture was stirred at room temperature for about 1 hour,TLC to monitor the complete conversion of the reaction.Rotary Evaporation In addition to solvent,The crude product was separated by silica gel column chromatography (petroleum ether / ethyl acetate = 10: 1, v / v)To give 301 mg of tert-butyl (4- (2-chloro-5-nitropyrimidine-4-amino) phenyl)carbamate as an orange solid in 82% yield.

The synthetic route of 71026-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; East China University of Science and Technology; LI, HONGLIN; XU, YUFANG; CHEN, ZHUO; ZHAO, ZHENJIANG; LU, JIANKUN; SUN, DEHENG; YANG, YU; ZHOU, WEI; (29 pag.)CN106467540; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 169556-48-3, name is N-Boc-DL-valinol, 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 169556-48-3, SDS of cas: 169556-48-3

General procedure: An aldehyde (30 mmol), Zn(OTf)2 (13 mg, 35 mmol), and (N-Chloroethyl)morpholine HCl 6.5 mg, 35 mmol) were added to a 1dram vial. The dry solvent, acetonitrile (1mL), was added to the vial. Afterwards dipicolylamine (7 muL 35 mmol) was added to the vial and the vial was sonicated. Once the solution was transparent molecular sieves were added to the solution along with the respective alcohol (175 mmol). The assemblies were incubated for 16 h at room temperature in the dark.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Minus, Matthew B.; Featherston, Aaron L.; Choi, Sooyun; King, Sam C.; Miller, Scott J.; Anslyn, Eric V.; Chem; vol. 5; 12; (2019); p. 3196 – 3206;,
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These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, 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. name: tert-Butyl (2-(benzylamino)ethyl)carbamate

Preparation 64: Synthesis of tert-butyl 2-(N-benzyl-N-methylamino)ethylcarbamate (B)To a cooled (~5 C) solution of compound A (6.2 g, 25.0 mmol) and TEA (3.0 g, 29.7 mmol, 4.13 mL) in chloroform (50 mL) was added iodomethane (4.2 g, 29.7 mmol, 1.85 mL). The pressure tube was sealed, and the mixture stirred at ambient temperature for 20 h. The mixture was then precipitated with ether (300 mL); the white solid was filtered off and washed with ether (50 mL). The filtrate was concentrated and the residual yellow oil (5.2 g) was purified by silica gel column chromatography (2-10% MeOH gradient in DCM) to give compound B (3.3 g, 12.5 mmol, 50%) as a colorless oil. TLC Rf (DCM/MeOH 9:1): 0.55. LC-MS [M+H] 264.3 (C15H24N2O2 +H, calc: 264.4).

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOFORE, INC.; JENKINS, Thomas, E.; HUSFELD, Craig, O.; SEROOGY, Julie, D.; WRAY, Jonathan, W.; WO2011/133150; (2011); A1;,
Amide – Wikipedia,
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Related Products of 216961-61-4, The chemical industry reduces the impact on the environment during synthesis 216961-61-4, name is tert-Butyl (10-aminodecyl)carbamate, I believe this compound will play a more active role in future production and life.

General procedure 2. Starting compound III: S-Methyl N-cyano-N’-(2-methyl4-pyridylisothiourea. Starting compound IV: 10-t-Butoxycarbonylaminodecylamine. Purification: Flash chromatography (Eluent 1% NH3(aq) and 0-10% MeOH in CH2Cl2). The compound was obtained as a yellow oil. 13C NMR (CDCl3) delta: 158.1, 157.3, 155.5, 149.4, 146.2, 116.5, 113.5, 112.0, 77.2, 41.7, 29.4, 28.9, 28.8, 28.6, 28.6, 28.6, 28.2, 26.2, 26.1, 24.0.

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 (10-aminodecyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Leo Pharmaceutical Products, Ltd. A/S; US6346520; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics