133010-01-2

Upstream product

• 4530-20-5 BOC-glycine 

Downstream Products

• 1058149-10-2 C₂₁H₃₂N₄O₆ 
• 500871-60-3 tert-butyl (2-(diethylamino)-2-oxoethyl)carbamate 
• 917252-92-7 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)glycyl)tetrahydrothiazole-4-carboxylate 
• 917253-03-3 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)glycyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 

Relevant academic research and scientific papers

Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride

Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

HETEROAROMATIC DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF

Provided herein are novel heteroaromatic derivatives, or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a prodrug, a pharmaceutically acceptable salt or a prodrug thereof, and pharmaceutical compositions containing such compounds. Also provided herein are uses of such compounds or pharmaceutical compositions thereof in the manufacture of a medicament for treating respiratory diseases, especially chronic obstructive pulmonary disease (COPD).

SUBSTITUTED HYDANTOINS

This invention relates to compounds of formula I: or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, and R6 are described in this application. These compounds inhibit the enzymes MEK 1 and MEK2, protein kinases that are components o

Effects of steric bulk and stereochemistry on the rates of?diketopiperazine formation from N-aminoacyl-2,2-dimethylthiazolidine-4-carboxamides (Dmt dipeptide amides)-a model for a new prodrug linker system

A peptide-like self-immolative molecular clip is required for release of active drugs from prodrugs by endopeptidases. Upon cleavage from the carrier, this clip must collapse and release the drug rapidly. A series of aminoacyl-5,5-dimethylthiaproline (Aaa

Synthesis of optically active C-allylglycine derivatives and conversion into isoquinolones

C-Allylglycyl amides can be efficiently synthesized via an auxiliary controlled diastereoselective aza-Claisen rearrangement. The stereodirecting unit is placed on an auxiliary derived from commercially available (S)-proline. After N-allylation, the obtained optically active allylamines were reacted with various N-protected glycyl fluorides to give the (2R)-C-allylglycyl amides in good yields. The diastereoselectivity of the asymmetric allylation varied between 1:1 and > 1:15 depending on the N-protective group, the auxiliary, and the reaction temperature. Likewise, the C-allylglycine derivatives can be used as monomers in peptide synthesis to synthesize (R)-proline derivatives or chiral isoquinolones; the latter should serve as building blocks in the total syntheses of alkaloids.

Synthesis of Boc- and Z-protected amino acid fluorides employing DAST as a fluorinating agent

DAST [(diethylamino)sulphur trifluoride] has been used as a fluorinating agent for the synthesis of Boc- and Z-protected amino acid fluorides. All the compounds made have been isolated as crystalline solids in good yield and purity.

New synthetic amino acids for the design and synthesis of peptide-based metal ion sensors

The syntheses of two new nonstandard amino acids, Flu (6) and XBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype for a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis

A new class of rapid-acting acylating agents, α-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid cyanuric fluoride.