28709-70-8

Usage

Chemical Properties

white powder

InChI:InChI=1/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/p-1/t15-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 1161-13-3 N-Cbz-L-Phe 
• 3588-57-6 Z-DL-Phe-OH 
• 541-41-3 chloroformic acid ethyl ester 
• 1609-47-8 diethyl dicarbonate 
• 74-96-4 ethyl bromide 
• 3338-39-4 N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 7663-85-6 N-(carbobenzyloxy)phenylalanine cyanomethyl ester 
• 2361-96-8 ethyl N-acetyl-(L)-phenylalaninate 
• 501-53-1 benzyl chloroformate 
• 16881-34-8 N-benzyloxycarbonyl-L-phenylalanine t-butyl ester 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 25613-61-0 4-Benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester 

Downstream Products

• 1161-13-3 N-Cbz-L-Phe 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 141056-54-4 N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalaninamide 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 100759-30-6 ethyl (S)-2-(ethylamino)-3-phenylpropanoate 
• 135219-73-7 (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester 
• 135219-45-3 (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester 
• 182742-42-3 (R)-2-[3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 72155-50-1 (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid 
• 132549-37-2 methyl (4S,5S)-4-benzyl-2-oxooxazolidine-5-acetate 
• 132549-32-7 (S)-((4S,5S)-4-Benzyl-2-oxo-oxazolidin-5-yl)-iodo-acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Nitrogen-Containing Heterocycles and Cyclopentenone Derivatives via Phosphine-Catalyzed Michael Addition/Intramolecular Wittig Reaction

The phosphine-catalyzed Michael addition/intramolecular Wittig reaction between dialkyl acetylenedicarboxylate and amino-carbaldehyde or amino ester derivatives has been developped. This reaction can be rendered catalytic in phosphine by the in situ chemoselective reduction of the phosphine oxide with silane. This methodology enables rapid access to a variety of nitrogen-containing heterocycles, which are present in numerous natural products and/or bioactive compounds. Either classical heating or microwave conditions give access to the desired products in good yields (15 examples, 60–99% yields). This catalytic methodology is further applicable to the synthesis of enantioenriched 1H-pyrrole derivatives, with the use of chiral phosphines. Finally, we successfully extended the reaction to the synthesis of a polysubstituted cyclopentenone, starting from butane-2,3-dione as substrate. (Figure presented.).

Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation

Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides. One of the main outcome of this work is the observation of a significant influence of the N-protecting group of the hemimalonate on its interaction with the catalyst. This methodology carried out under mild conditions exhibits good substrate scope and functional group tolerance. A substoichiometric amount of catalyst can also be used in certain cases while affording good yields and selectivities.

COMPOUNDS USEFUL AS CSF1 MODULATORS

This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.

Solventless mechanosynthesis of N-protected amino esters

Mechanochemical derivatizations of N- or C-protected amino acids were performed in a ball mill under solvent-free conditions. A vibrational ball mill was used for the preparation of N-protected α- and β-amino esters starting from the corresponding N-unmasked precursors via a carbamoylation reaction in the presence of di-tert-butyl dicarbonate (Boc2O), benzyl chloroformate (Z-Cl) or 9-fluorenylmethoxycarbonyl chloroformate (Fmoc-Cl). A planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.

Fully enzymatic N→C-directed peptide synthesis using C-terminal peptide α-carboxamide to ester interconversion

Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required and racemisation does not occur rendering purification easier compared to chemical peptide synthesis. In this paper, a novel interconversion reaction of peptide C-terminal α-carboxamides into primary alkyl esters with alcalase was used to develop a fully enzymatic peptide synthesis strategy. For each elongation step a cost-efficient amino acid carboxamide building block was used followed by the interconversion of the elongated peptide carboxamide to the corresponding primary alkyl ester. These peptide esters are the starting materials for the next enzymatic peptide elongation step. Copyright

Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles

Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.

Fully enzymatic peptide synthesis using C-terminal tert-butyl ester interconversion

Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required an

Versatile selective α-carboxylic acid esterification of N-protected amino acids and peptides by alcalase

Under continuous removal of water, the industrial protease Alcalase allows selective synthesis of α-carboxylic acid methyl, ethyl, benzyl, allyl, 2-(trimethylsilyl)ethyl, and tert-butyl esters of amino acids and peptides under mild conditions in very high

A facile deprotection of secondary acetamides

(Chemical Equation Presented) Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, can be harnessed for a selective and practical deprotection sequence. Treatment of these intermediates with 2 equiv of propylene glycol and warming enables the rapid release of amine hydrochloride salts in good yields. Notably, the reaction conditions are mild enough to allow for a swift deprotection with no observed epimerization of the amino center.

Structure-activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling

Endomorphin-2 (EM-2) is a putative endogenous μ-opioid receptor ligand. To get insight into the important role of C-terminal amide group of EM-2, we investigated herein a series of EM-2 analogs by substitution of the C-terminal amide group with -NHNH2, -NHCH3, -N(CH3)2, -OCH3, -OCH2CH3, -OC(CH3)3, and -CH2-OH. Their binding affinity and bioactivity were determined and compared. Despite similar (analogs 1, 4, and 7) or decreased (analogs 2, 3,5, and 6) μ affinity in binding assays, all analogs showed low guinea pig ileum (GPI) and mouse vas deferens (MVD) potencies compared to their parent peptide. Interestingly, as for analogs 2 and 3 (a single and double N-methylation of C-terminal amide), the potency order with the Ki (μ) values was 2 > 3; for the C-terminal esterified analogs 4-6, the potency order with the Ki (μ) values was 4 > 5 > 6. Thus, we concluded that the steric hindrance of C-terminus might play an important role in opioid receptor affinity. We further investigated the conformational properties of these analogs by 1D and 2D 1H NMR spectroscopy and molecular modeling. Evaluating the ratios of cis- and trans-isomers, aromatic interactions, dihedral angles, and stereoscopic views of the most convergent conformers, we found that modifications at the C-terminal amide group of EM-2 affected these analog conformations markedly, therefore changed the opioid receptor affinity and in vitro bioactivity.