68709-71-7

Upstream product

• 85613-64-5 (S)-3-(tert-butoxycarbonyl)amino-4-phenyl-2-butanone 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 74-95-3 1,1-dibromomethane 
• 186581-53-3 diazomethane 

Downstream Products

• 388073-12-9 C₂₂H₂₉IN₂O₃ 
• 1361944-81-1 C₃₂H₄₀IN₃O₃ 
• 1375000-10-4 C₃₀H₃₅N₅O₈ 
• 1375000-16-0 C₂₂H₂₉N₅O₆ 
• 1402730-08-8 C₁₆H₂₂N₄O₂ 
• 1237501-99-3 C₁₈H₂₂N₄O₅ 
• 1237501-81-3 Boc-Phe-CH₂N₃ 
• 118405-09-7 [(S)-1-Benzyl-4-{(S)-1-[(S)-2-((S)-1-benzylcarbamoyl-3-methyl-butylcarbamoyl)-1-hydroxy-ethyl]-3-methyl-butylcarbamoyl}-2-hydroxy-5-(1H-imidazol-4-yl)-pentyl]-carbamic acid tert-butyl ester 
• 124339-04-4 Boc-PheΨGly-Sta-Leu-NHCH2Ph 
• 118388-87-7 2-((S)-3-tert-Butoxycarbonylamino-2-oxo-4-phenyl-butyl)-2-(1H-imidazol-4-ylmethyl)-malonic acid dibenzyl ester 
• 68709-76-2 5(S)-<(butyloxycarbonyl)amino>-6-phenyl-4-oxohexanoic acid 
• 136630-90-5 2-<<<(4S,5R)-4-benzyl-2,2-dimethyl-5-oxazolidinyl>methyl>thio>acetic acid 
• 136630-91-6 2-<<<(4S,5S)-4-benzyl-2,2-dimethyl-5-oxazolidinyl>methyl>thio>acetic acid 

Relevant academic research and scientific papers

One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones

A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.

CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click react

Synthesis of N-urethane protected α-aminoalkyl-α-cyanomethyl ketones; Application to the synthesis of 3-substituted 5-amino-1H-pyrazole tethered peptidomimetics

The preparation of N-protected amino/peptide α-cyanomethyl ketones through cyanation of the corresponding α-bromomethyl ketones is described. The utility of the resulting α-cyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the α-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected d- and l-Ala-OH as model substrates. The synthesis of peptide pyrazolecarboxamides is also delineated. Georg Thieme Verlag Stuttgart · New York.

Design, synthesis, and biological evaluation of novel fluorinated ethanolamines

The preparation of novel fluorinated allylamines and their use as key fragments for the stereoselective synthesis of hydroxyethyl secondary amine (HEA)-type peptidomimetics is described. Our strategy employs chiral sulfinyl imines as synthesis intermediates, by treatment of hemiaminal precursors with two equivalents of vinylmagnesium bromide. The subsequent oxidation of the allylic amines to the corresponding epoxides was achieved by treatment with methyl(trifluoromethyl)dioxirane. Finally, epoxide ring opening with a range of nitrogen nucleophiles provided a library of HEA-derived peptidomimetics with a phenyldifluoromethylene moiety. The biological evaluation of these derivatives revealed compounds with remarkable BACE1 inhibitory activity. Docking studies revealed the influence of the fluorine atoms in the binding mode of the synthesized ligands. Furthermore, the biological evaluation of our final products and synthesis intermediates led to the discovery of compounds with antimicrobial activity against Mycobacterium and Nocardia species.

Amino acid derived epoxide ring opening under microwave irradiation

A solvent-free microwave-assisted methodology for the obtainment of the hydroxyethylamine (HEA) isostere is described. A phenylalanine derived aminoalkyl epoxide is allowed to react with a dipeptide amine using basic alumina partially deactivated with water under microwave irradiation. The HEA is obtained in very short time (3 min). This methodology is amenable to application in a parallel or automatic sequential format. Copyright

Design, synthesis, and evaluation of inhibitors for severe acute respiratory syndrome 3C-like protease based on phthalhydrazide ketones or heteroaromatic esters

The 3C-like protease (3CLpro), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CLpro inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.

PROCESS FOR PRODUCING ALPHA-AMINOHALOMETHYL KETONE DERIVATIVES

Herein is disclosed a process for producing an α-aminohalomethyl ketone derivative which comprises subjecting to catalytic reduction the corresponding α-aminodihalomethyl ketone derivative, and which process is efficient and suited for industrial production thereof.

Process for producing alpha-aminohalomethyl ketone derivatives

Herein is disclosed a process for producing an α-aminohalomethyl ketone derivative which comprises subjecting to catalytic reduction the corresponding α-aminodihalomethyl ketone derivative, and which process is efficient and suited for industrial production thereof.

Dihalomethylation of N-protected phenylalanine esters

Dihalomethylation of several N-protected amino acid esters gave N-protected α-aminoalkyl-α′-dihalomethylketones, which are useful intermediates for the synthesis of erythro β-amino-α-hydroxycarboxylic acids, in good yield. The dihalomethylketones were successfully converted to N-protected α-aminoalkyl-α′-halomethylketones by selective catalytic hydrogenation.

Stereoselective synthesis of erythro α-amino epoxides

The stereoselective reduction of bromomethyl ketones derived from leucine, phenylalanine, alanine and valine is described using borohydride reagents. The Boc-amino alcohol product has erythro stereochemistry at the carbinol center as deduced by conversion to Boc-amino epoxides. These oxiranes are useful for the preparation of hydroxyethylene peptide isosteres.