174174-66-4

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 133287-30-6 (S)-2-amino-3-phenyl-N-[(R)-1-phenylethyl]propanamide 
• 174007-73-9 {(R)-2-(1-Formyl-1H-indol-3-yl)-1-[(S)-2-phenyl-1-((R)-1-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 174007-77-3 ((1S,2R)-1-{(R)-2-(1-Formyl-1H-indol-3-yl)-1-[(S)-2-phenyl-1-((R)-1-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-ethylcarbamoyl}-2-hydroxy-propyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination

We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.

Direct amidation of amino acid derivatives catalyzed by arylboronic acids: Applications in dipeptide synthesis

The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered. Arylboronic acids can be used to catalyze the direct amide formation of protected amino acid derivatives. For less reactive amino acids, cooperative catalysis can be used involving two arylboronic acids, one electron-rich and one electron-deficient, at high catalyst loadings to give good conversions at moderate temperatures. Copyright

Synthesis of optically active γ-valerolactone and γ-nonanolactone via optical resolution using chiral amine derived from amino acid

Optically active γ-valerolactone and γ-nonanolactone have been synthesized via optical resolution using a newly developed chiral amine derived from L-phenylalanine. Both racemic γ-lactones were transformed to corresponding diastereomeric amides by amidation with the optical resolution agent. Fractional crystallization of diastereomeric amides, recrystallization of each diastereomer, and subsequent hydrolysis gave optically active γ-valerolactone and γ-nonanolactone with sufficient enantiomeric excess and isolated yield. The optical resolution agent was recovered after hydrolysis.

Efficient preparation of chiral diamines via Red-Al reduction of N-Boc-protected amino acid-derived secondary amides

Conditions have been developed for the selective reduction of N-Boc-protected amino acid-derived secondary amides, avoiding the formation of overreduction and cyclic urea byproducts. The method is showcased by the efficient formal synthesis of NK-1 antagonist LY303870.

Preparation of polymer-bound pyrazolone active esters for combinatorial chemistry

The preparation of solid-phase active esters from a new pyrazolone linker resin is described. N-Acylation using this resin provides various amide products with a high conversion rate and good purity under mild conditions. The polymer-bound pyrazolone linkers are stable in the reaction conditions and are resistant to hydrolysis. Moreover, this resin can also be reused repeatedly without a loss of reactivity.

Synthesis and in vitro activities of highly potent and selective tripeptide antagonists of the neurokinin NK-1 receptor

We report on the synthesis and the pharmacological properties of a new series of tachykinin antagonists based on the tripeptide Ac-Thr-D-Trp(CHO)-Phe-N(Me)-Bzl (1, FR113680) partly modified on the C-terminal amide part. Stereochemistry around the benzilic