Category: amides-buliding-blocks

Chakraborty, Moubani; Haag, Stephanie L.; Bernards, Matthew T.; Waynant, Kristopher V. published an article in 2021. The article was titled 《Synthesis of a zwitterionic N-Ser-Ser-C dimethacrylate cross-linker and evaluation in polyampholyte hydrogels》, and you may find the article in Biomaterials Science.Name: tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

Polyampholyte hydrogels are attractive materials for tissue engineering scaffolds as they offer a wide variety of features including nonfouling, selective protein delivery, and tunable phys. characteristics. However, to improve the potential performance of these materials for in vivo applications, there is a need for a higher diversity of zwitterionic cross-linker species to replace commonly used ethylene glycol (EG) based chemistries. Toward this end, the synthesis of a dipeptide based zwitterionic cross-linker, N-Ser-Ser-C dimethacrylate (S-S) from N-Boc-L-serine is presented. The strategy utilized a convergent coupling of methacrylated serine partners followed by careful global deprotection to yield the zwitterionic cross-linker with good overall yields. This novel cross-linker was incorporated into a polyampholyte hydrogel and its phys. properties and biocompatibility were compared against a polyampholyte hydrogel synthesized with an EG-based cross-linker. The S-S cross-linked hydrogel demonstrated excellent nonfouling performance, while promoting enhanced cellular adhesion to fibrinogen delivered from the hydrogel. Therefore, the results suggest that the S-S cross-linker will demonstrate superior future performance for in vivo applications. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Name: tert-Butyl N,N’-diisopropylcarbamimidate)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Name: tert-Butyl N,N’-diisopropylcarbamimidate

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Sun, Bin; Tang, Xiaoli; Shi, Rongcheng; Yan, Zhiyang; Li, Bingqian; Tang, Chen; Jin, Can; Wu, Chunlei L.; Shen, Runpu P. published their research in Asian Journal of Organic Chemistry in 2021. The article was titled 《Self-photocatalyzed Homolytic Dehalogenative Alkylation/Cyclization of Unactivated Alkenes Based on the Quinazolinone Skeleton via Energy Transfer》.Recommanded Product: 2-Bromoacetamide The article contains the following contents:

A mild, external photocatalyst- and additive-free protocol for photo-induced alkylation/cyclization of unactivated alkenes with halides has been developed. This strategy showed excellent regioselectivity and simple operation to synthesize alkyl-substituted quinazolinones with a broad substrate scope. More importantly, chlorinated alkanes were also compatible with this transformation. In the experiment, the researchers used 2-Bromoacetamide(cas: 683-57-8Recommanded Product: 2-Bromoacetamide)

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Recommanded Product: 2-Bromoacetamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Engaging Sulfonamides: Intramolecular Cross-Electrophile Coupling Reaction of Sulfonamides with Alkyl Chlorides》 was published in Journal of Organic Chemistry in 2020. These research results belong to Lucas, Erika L.; Hewitt, Kirsten A.; Chen, Pan-Pan; Castro, Anthony J.; Hong, Xin; Jarvo, Elizabeth R.. Recommanded Product: 4-Methylbenzenesulfonamide The article mentions the following:

The application of amine derivatives as coupling partners is rare due to the inherent strength of the C-N bond. Herein, the first cross-electrophile coupling reaction of unstrained benzylic sulfonamides is repoted. Nickel-catalyzed intramol. cross-electrophile coupling reactions of acyclic and cyclic benzylic sulfonamides with pendant alkyl chlorides generate cyclopropane products. Mechanistic experiments and DFT calculations are consistent with initiation of the reaction by magnesium iodide accelerated oxidative addition of the benzylic sulfonamide. This work establishes neutral and unstrained amine derivatives as XEC partners, furnishes structural rearrangement of benzylic sulfonamides, and provides valuable information regarding catalyst design for the development of new cross-electrophile coupling reactions of carbon-heteroatom bonds. The results came from multiple reactions, including the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3Recommanded Product: 4-Methylbenzenesulfonamide)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Recommanded Product: 4-Methylbenzenesulfonamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2018,Yu, Chang-Bin; Wang, Jie; Zhou, Yong-Gui published 《Facile synthesis of chiral indolines through asymmetric hydrogenation of in situ generated indoles》.Organic Chemistry Frontiers published the findings.Name: N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

A concise and enantioselective procedure for the synthesis of optically active indolines I [R = Me, n-Bu, Bn, etc.; R1 = H, 2-Me, 2-OMe, 4-OMe, 2,4-di-Me] was developed through intramol. condensation, deprotection and palladium-catalyzed asym. hydrogenation in a one-pot process with up to 96% ee. A strong Bronsted acid played an important role in both the formation of indoles and asym. hydrogenation process. This strategy could be scaled-up with excellent reactivity and enantioselectivity. The results came from multiple reactions, including the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1Name: N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Name: N-Methoxy-N-methylacetamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2016,Yang, Xing; Mease, Ronnie C.; Pullambhatla, Mrudula; Lisok, Ala; Chen, Ying; Foss, Catherine A.; Wang, Yuchuan; Shallal, Hassan; Edelman, Hannah; Hoye, Adam T.; Attardo, Giorgio; Nimmagadda, Sridhar; Pomper, Martin G. published 《[18F]Fluorobenzoyllysinepentanedioic Acid Carbamates: New Scaffolds for Positron Emission Tomography (PET) Imaging of Prostate-Specific Membrane Antigen (PSMA)》.Journal of Medicinal Chemistry published the findings.Product Details of 71432-55-8 The information in the text is summarized as follows:

Radiolabeled urea-based low-mol. weight inhibitors of the prostate-specific membrane antigen (PSMA) are under intense investigation as imaging and therapeutic agents for prostate and other cancers. In an effort to provide agents with less nontarget organ uptake than the ureas, we synthesized four 18F-labeled inhibitors of PSMA based on carbamate scaffolds. 4-Bromo-2-[18F]fluorobenzoyllysineoxypentanedioic acid (OPA) carbamate and 4-iodo-2-[18F]fluorobenzoyllysine OPA carbamate (I) in particular exhibited high target-selective uptake in PSMA+ PC3 PIP tumor xenografts, with tumor-to-kidney ratios of >1 by 4 h postinjection, an important benchmark. Because of its high tumor uptake (90% injected dose per g of tissue at 2 h postinjection) and high tumor-to-organ ratios, I (X=Br) is promising for clin. translation. Prolonged tumor-specific uptake demonstrated by I (X=I), which did not reach equilibrium during the 4 h study period, suggests carbamates as alternative scaffolds for mitigating dose to nontarget tissues. The results came from multiple reactions, including the reaction of tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Product Details of 71432-55-8)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Product Details of 71432-55-8

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2016,Gao, Shang; Wu, Zijun; Wu, Fei; Lin, Aijun; Yao, Hequan published 《Catalyst-Controlled Regiodivergent Dehydrogenative Heck Reaction of 4-Arylthiophene/Furan-3-Carboxylates》.Advanced Synthesis & Catalysis published the findings.Related Products of 78191-00-1 The information in the text is summarized as follows:

A catalyst-controlled regiodivergent dehydrogenative Heck reaction of 4-arylthiophene/furan-3-carboxylates has been realized. Use of a palladium catalyst led to the C-5 alkenylation through electronic palladation to afford, e.g., I, while a ruthenium catalyst favored the C-2 alkenylation with the assistance of a directing group to yield, e.g., II. This reaction exhibited good to excellent regioselectivities. The experimental process involved the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1Related Products of 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Related Products of 78191-00-1

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2013,Zeller, Wayne E. published 《Synthesis of (+)- and (-)-Phaselic Acid》.Synthetic Communications published the findings.Reference of tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

The syntheses of both enantiomers of phaselic acid (2-O-caffeoylmalate) are described. The previously unreported acetate-protected caffeic acid anhydride was used with appropriately protected malic acid derivatives as coupling partners to provide fully protected phaselic acid. Sequential unmasking of the protecting groups afforded phaselic acid in an acceptable overall yield. Supplemental materials are available for this article. Go to the publisher’s online edition of Synthetic Communications to view the free supplemental file. In the experiment, the researchers used many compounds, for example, tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Reference of tert-Butyl N,N’-diisopropylcarbamimidate)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Reference of tert-Butyl N,N’-diisopropylcarbamimidate

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Soley, Jacob; Taylor, Scott D. published an article on February 21 ,2020. The article was titled 《Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols》, and you may find the article in Journal of Organic Chemistry.Recommanded Product: H-Lys(Boc)-OH The information in the text is summarized as follows:

The 9-phenyl-9-fluorenyl (PhF) group has been used as an Nα protecting group of amino acids and their derivatives mainly as a result of its ability to prevent racemization. However, installing this group using the standard protocol, which employs 9-bromo-9-phenylfluorene/K3PO4/Pb(NO3)2, often takes days and yields can be variable. Here, we demonstrate that the PhF group can be introduced into the amino group of Weinreb’s amides and Me esters of amino acids, as well as into alcs. and carboxylic acids, rapidly and in excellent yields, using 9-chloro-9-phenylfluorene (PhFCl)/N-methylmorpholine (NMM)/AgNO3. Nα-PhF-protected amino acids can be prepared from unprotected α-amino acids, rapidly and often in near quant. yields, by treatment with N,O-bis(trimethylsilyl)acetamide (BSA) and then PhFCl/NMM/AgNO3. Primary alcs. can be protected with the PhF group in the presence of secondary alcs. in moderate yield. Using PhFCl/AgNO3, a primary alc. can be protected in good yield in the presence of a primary ammonium salt or a carboxylic acid. Primary sulfonamides and amides can be protected in moderate to good yields using phenylfluorenyl alc. (PhFOH)/BF3·OEt2/K3PO4, while thiols can be protected in good to excellent yield using PhFOH/BF3·OEt2 even in the presence of a carboxylic acid or primary ammonium group. The results came from multiple reactions, including the reaction of H-Lys(Boc)-OH(cas: 2418-95-3Recommanded Product: H-Lys(Boc)-OH)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. In addition to subunits of proteins, amino acids have many other functions as well, including osmoregulation (proline), neurotransmitters (gamma-aminobutyric acid), metabolic intermediates (ornithine and citrulline), and inhibitors (dehydroproline).Recommanded Product: H-Lys(Boc)-OH

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Bohnstedt, Adolph C.; Prasad, J. V. N. Vara; Rich, Daniel H. published their research in Tetrahedron Letters on August 13 ,1993. The article was titled 《Synthesis of E- and Z-alkene dipeptide isosteres》.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The article contains the following contents:

The syntheses of MeLeu-Leu and MeLeu-D-Leu alkene dipeptide isosteres (E)-I and (E)-II (Boc = Me3CO2C, R = H), and (Z)-I and (Z)-II (R = Me) are described. (E)-I and (E)-II were synthesized stereoselectively by employing the [2,3]-Wittig rearrangement to control double bond geometry and C-2 configuration. (Z)-I and (Z)-II were obtained as an easily separable mixture of diastereomers via alkylation of a Z-alkene MeLeu-Gly isostere that was obtained using a Z-selective Wittig reaction as the key step. All isosteres are isolated with high stereochem. purity. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of C13H26N2O4On March 31, 1999, Llinares, M.; Devin, C.; Chaloin, O.; Azay, J.; Noel-Artis, A.-M.; Bernad, N.; Fehrentz, J.-A.; Martinez, J. published an article in Journal of Peptide Research. The article was 《Syntheses and biological activities of potent bombesin receptor antagonists》. The article mentions the following:

Bombesin receptor antagonists are potential therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis concerning the mechanism of action of gastrin associating an activating enzyme to the receptor and on the results reported in the literature, we have synthesized bombesin analogs which have been modified in the C-terminal part. Potent bombesin receptor antagonists were obtained by replacement of Leu-13 with a statyl residue or with a residue bearing an hydroxyl group in place of the carbonyl function of Leu-13. Several inhibitors were able to recognize the bombesin receptor on rat pancreatic acini and antagonized bombesin stimulated amylase secretion in the nano-molar range. These compounds were also able to recognize the bombesin receptor and to inhibit [3H] thymidine incorporation in 3T3 cells with the same potency. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Electric Literature of C13H26N2O4 Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics