- Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
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Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.
- Sabatini, Marco T.,Karaluka, Valerija,Lanigan, Rachel M.,Boulton, Lee T.,Badland, Matthew,Sheppard, Tom D.
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supporting information
p. 7033 - 7043
(2018/05/04)
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- Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids
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(S)-4-(3-Aminopyrrolidin-1-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-1-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable 1H NMR optical purity determination agents for chiral carboxylic acids.
- Wada, Koji,Goto, Mizuko,Yamashita, Hiroshi,Nagasawa, Kazuo
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p. 964 - 978
(2017/06/13)
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- SYNTHESIS OF CAPROLACTAM FROM LYSINE
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In various embodiments, the present invention can involve a method of synthesizing α-amino-ε -caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ε-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce α-amino -ε- caprolactam, deaminating to produce ε-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention can include methods of making nylon 6. The methods can comprise synthesizing ε-caprolactam and then polymerizing, wherein the ε--caprolactam is derived from L-lysine.
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Page/Page column 7-8
(2008/06/13)
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- ANTI-INFLAMMATORY AGENTS
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The invention relates to the use of 3-aminocaprolactam derivatives for preparing a medicament intended to prevent or treat inflammatory disorders, and uses compounds of general formula (I) or a pharmaceutically acceptable salts thereof; wherein X is -CO-R1 or-S02-R2, and R1 and R2 are carbonaceous substituents.
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Page/Page column 16
(2010/02/11)
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