158744-36-6Relevant academic research and scientific papers
An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives
Honda, Yutaka,Katayama, Satoshi,Kojima, Mitsuhiko,Suzuki, Takayuki,Izawa, Kunisuke
, p. 3163 - 3166 (2003)
Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding β-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This inte
New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds
Alongi, Maddalena,Minetto, Giacomo,Taddei, Maurizio
, p. 7069 - 7072 (2007/10/03)
A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides.
Process for producing 3-amino-2-oxo-1-halogenopropane derivatives
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, (2008/06/13)
Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.
Synthesis of N-protected γ-amino-β-keto-esters from urethane N-carboxyanhydrides (UNCAs)
Paris, Marielle,Fehrentz, Jean-Alain,Heitz, Annie,Loffet, Albert,Martinez, Jean
, p. 8489 - 8492 (2007/10/03)
N-protected γ-amino-β-keto-esters were synthesized from the corresponding N-protected N-carboxyanhydride (UNCAs) by reaction with the lithium enolate of ethyl acetate in good yields. These compounds are precursors of statine derivatives.
The Reformatsky Reaction of 1-Acyl-3,5-dimethylpyrazoles. A Convenient Preparation of 4-Amino-3-oxoalkanoic Acid Derivatives
Kashima, Choji,Kita, Isanobu,Takahashi, Katsumi,Hosomi, Akira
, p. 723 - 726 (2007/10/02)
The conversion of N-acylpyrazoles into β-keto esters was accomplished efficiently by the treatment with α-bromo esters and zinc dust.Using this Reformatsky reaction of N-acylpyrazoles, 4-(protected amino)-3-oxoalkanoic acid derivatives were conveniently prepared as the key intermediates in the synthesis of statines.
Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959
Parkes, Kevin E. B.,Bushnell, David J.,Crackett, Peter H.,Dunsdon, Stephen J.,Freeman, Andrew C.,et al.
, p. 3656 - 3664 (2007/10/02)
Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials.Six approaches for the large-scale synthesis of this compound have been studied.All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5.They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation.The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1.Kilogram quantities of Ro 31-8959 have been prepared using this route.
