Category: 87694-50-6

《Continuous process improvement in the manufacture of carfilzomib. Part 1: Process understanding and improvements in the commercial route to prepare the epoxyketone warhead》 was written by Dornan, Peter K.; Anthoine, Travis; Beaver, Matthew G.; Cheng, Guilong Charles; Cohen, Dawn E.; Cui, Sheng; Lake, William E.; Langille, Neil F.; Lucas, Susan P.; Patel, Jenil; Powazinik, William; Roberts, Scott W.; Scardino, Chris; Tucker, John L.; Spada, Simone; Zeng, Alicia; Walker, Shawn D.. Formula: C13H26N2O4 And the article was included in Organic Process Research & Development on April 17 ,2020. The article conveys some information:

In the first case study, the mechanism of racemization of an α-chiral enone was investigated, resulting in the development of an improved aqueous workup procedure. Next, the stability of a bleach/pyridine mixture used for the step 3 epoxidation reaction was studied, leading to the identification of pyridine as a key raw material and improved reaction conditions and control strategy to meet the conversion target. Finally, oxidized butylated hydroxytoluene (oBHT) was identified as an impurity arising from the use of BHT-stabilized THF in steps preceding the oxidation The process understanding obtained from these investigations have led to the implementation of process improvements which improve the robustness of the process. The development of a second-generation route to epoxyketone I was the subject of the second manuscript in this series. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. 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.Formula: C13H26N2O4

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

《Design of potent inhibitors for human brain memapsin 2 (β-secretase)》 was written by Ghosh, Arun K.; Shin, Dongwoo; Downs, Debbie; Koelsch, Gerald; Lin, Xinli; Ermolieff, Jacques; Tang, Jordan. Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide And the article was included in Journal of the American Chemical Society on April 12 ,2000. The article conveys some information:

Two highly potent inhibitors of human memapsin 2 were designed and synthesized from current available specificity information. The inhibitors, OM99-1 and OM99-2, were tested for inhibition of recombinant human memapsin 2 prepared from E. coli expression. In the part of experimental materials, we found many familiar compounds, such as (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Reference of (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. 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. Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

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

Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn May 10, 2012 ,《Small Molecule Suppression of Carbapenem Resistance in NDM-1 Producing Klebsiella pneumoniae》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Worthington, Roberta J.; Bunders, Cynthia A.; Reed, Catherine S.; Melander, Christian. The article conveys some information:

The already considerable global public health threat of multidrug-resistant Gram-neg. bacteria has become even more of a concern following the emergence of New Delhi metallo-β-lactamase (NDM-1) producing strains of Klebsiella pneumoniae and other Gram-neg. bacteria. As an alternative approach to the traditional development of new bactericidal entities, we have identified a 2-aminoimidazole-derived small mol. that acts as an antibiotic adjuvant and is able to suppress resistance of a NDM-1 producing strain of K. pneumoniae to imipenem and meropenem, in addition to suppressing resistance of other β-lactam nonsusceptible K. pneumoniae strains. The small mol. is able to lower carbapenem min. inhibitory concentrations by up to 16-fold, while exhibiting little bactericidal activity itself. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application In Synthesis of (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.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide 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

Almaliti, Jehad; Miller, Bailey; Pietraszkiewicz, Halina; Glukhov, Evgenia; Naman, C. Benjamin; Kline, Toni; Hanson, Jeffrey; Li, Xiaofan; Zhou, Sihong; Valeriote, Frederick A.; Gerwick, William H. published an article in European Journal of Medicinal Chemistry. The title of the article was 《Exploration of the carmaphycins as payloads in antibody drug conjugate anticancer agents》.Quality Control of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The author mentioned the following in the article:

Antibody-drug conjugates (ADCs) represent a new dimension of anticancer chemotherapeutics, with warheads to date generally involving either antitubulin or DNA-directed agents to achieve low-to sub-nanomolar potency. However, other potent cytotoxins working by different pharmacol. mechanisms are under investigation, such as α,β-epoxyketone based proteasome inhibitors. These proteasome active agents are an emerging class of anticancer drug that possesses ultra-potent cytotoxicity to some cancer cell lines. The carmaphycins are representatives of this latter class that we isolated and characterized from a marine cyanobacterium, and these as well as several synthetic analogs exhibit this level of potency. In the current work, we investigated the use of these highly potent cytotoxic compounds as warheads in the design of novel ADCs. We designed and synthesized a library of carmaphycin B analogs that contain amine handles, enabling their attachment to an antibody linker. The basicity of these incorporated amine handles was shown to strongly affect their cytotoxic properties. Linear amines resulted in the greatest reduction in cytotoxicity whereas less basic aromatic amines retained potent activity as demonstrated by a 4-sulfonylaniline derivative These investigations resulted in identifying the P2 residue in the carmaphycins as the most suitable site for linker attachment point, and hence, we synthesized a highly potent analog of carmaphycin B that contained a 4-sulfonylaniline handle as an attachment point for the linker antibody. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Quality Control of (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. 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.Quality Control of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

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

Hooper, Joel F.; Seo, Sangwon; Truscott, Fiona R.; Neuhaus, James D.; Willis, Michael C. published an article on February 10 ,2016. The article was titled 《α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation》, and you may find the article in Journal of the American Chemical Society.SDS of cas: 87694-50-6 The information in the text is summarized as follows:

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6SDS of cas: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.SDS of cas: 87694-50-6

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

Lescop, Cyrille; Herzner, Holger; Siendt, Herve; Bolliger, Reto; Henneboehle, Marco; Weyermann, Philipp; Briguet, Alexandre; Courdier-Fruh, Isabelle; Erb, Michael; Foster, Mark; Meier, Thomas; Magyar, Josef P.; Von Sprecher, Andreas published their research in Bioorganic & Medicinal Chemistry Letters on December 1 ,2005. The article was titled 《Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy》.Electric Literature of C13H26N2O4 The article contains the following contents:

Dipeptide-derived α-keto-amide compounds, e.g., I, with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown pos. effects on histol. parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. In the part of experimental materials, we found many familiar compounds, such as (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. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. 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. Electric Literature of C13H26N2O4

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

HPLC of Formula: 87694-50-6On May 5, 1998 ,《The design and synthesis of inhibitors of the cysteinyl protease, Der p I》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Billson, Jeremy; Clark, Jonathan; Conway, Simon P.; Hart, Terance; Johnson, Tony; Langston, Steven P.; Ramjee, Manoj; Quibell, Martin; Scott, Richard K.. The article conveys some information:

Prototype irreversible inhibitors I [R = H, Me3CO2C (Boc), Ac, Bz, R1 = CO2Et; R = Boc, R1 = SO2Me, SO2CH2Ph, SO2Ph] and II (R2 = H, Me, Cl, CF3) of the cysteinyl protease Der p I were designed, synthesized and evaluated in vitro. Candidates were designed using a modular approach, whereby a peptide sequence was appended with known thiophilic moieties. This hinged on utilizing peptide sequences from substrate specificity data compiled using proprietary RAPiD technol. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6HPLC of Formula: 87694-50-6)

(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. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.HPLC of Formula: 87694-50-6 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

《Continuous process improvement in the manufacture of carfilzomib, part 2: An improved process for synthesis of the epoxyketone warhead》 was written by Beaver, Matthew G.; Shi, Xianqing; Riedel, Jan; Patel, Parth; Zeng, Alicia; Corbett, Michael T.; Robinson, Jo Anna; Parsons, Andrew T.; Cui, Sheng; Baucom, Kyle; Lovette, Mike; Icten, Elcin; Brown, Derek B.; Allian, Ayman; Flick, Tawnya G.; Chen, Wendy; Yang, Ning; Walker, Shawn D.. Application of 87694-50-6 And the article was included in Organic Process Research & Development on April 17 ,2020. The article conveys some information:

The development and kilogram-scale demonstration of an improved process for the synthesis of the epoxyketone warhead of carfilzomib is described. Critical to the success of this process was: (1) development of a scalable asym. epoxidation protocol; (2) identification of a crystalline intermediate with improved phys. properties for isolation; (3) discovery and optimization of epimerization conditions to set the target stereochem.; and (4) introduction of a seeded-bed coaddn. crystallization to facilitate isolation of the final low-melting target. The results of kilogram-scale demonstration runs are shared, including details of a continuous process for the safe execution of an exothermic Barbier-type Grignard process. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application of 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. 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.Application of 87694-50-6

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

《1,2,3-Triazoles as Amide Bond Mimics: Triazole Scan Yields Protease-Resistant Peptidomimetics for Tumor Targeting》 was published in Angewandte Chemie, International Edition in 2013. These research results belong to Valverde, Ibai E.; Bauman, Andreas; Kluba, Christiane A.; Vomstein, Sandra; Walter, Martin A.; Mindt, Thomas L.. Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The article mentions the following:

The authors report a “”triazole-based scan”” of a bombesin peptide fragment, [Nle14]-BBN(7-14), for identifying novel peptidomimetics with improved properties. Using click chem.-based synthetic strategy, a triazole replacement for the peptide bond was incorporated into the above bombesin peptide fragment, and this led to the synthesis of a series of peptide-based radiotracers with retained nanomolar receptor affinity and an up-to-five fold improved serum stability. In vivo evaluation of a backbone-modified peptide analogs demonstrated the enhanced stability of the vector and its improved tumor-targeting capability. The authors expect that this new methodol. for the stabilization of peptides will find broader application in the field of tumor targeting with small peptides for drug delivery, imaging and peptide receptor radiotherapy. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide) was used in this study.

(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. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide 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

《Proteasome selectivity towards Michael acceptor containing oligopeptide-based inhibitors》 was written by van der Linden, Wouter A.; Geurink, Paul P.; Oskam, Chris; van der Marel, Gijsbert A.; Florea, Bogdan I.; Overkleeft, Herman S.. COA of Formula: C13H26N2O4 And the article was included in Organic & Biomolecular Chemistry on April 21 ,2010. The article conveys some information:

The synthesis and biol. evaluation of ten Michael acceptors containing potential proteasome inhibitors are described. Cellular targets of azide containing inhibitors Ib and VIIIb were assessed in HEK293T and RAW264.7 cells by a two step labeling strategy, followed by biotin-pulldown, affinity purification, on-bead tryptic digestion and LC-MS2 identification. This strategy appears to be an attractive alternative to gel-based competition assays. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6COA of Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.COA of Formula: C13H26N2O4Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis.

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