26081-07-2

Usage

Uses

Used in Pharmaceutical Industry:
L(-)-ALPHA-AMINO-EPSILON-CAPROLACTAM is used as a key intermediate in the total synthesis of bengamides. Bengamides are a group of bioactive compounds naturally found in marine sponges, known for their diverse range of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties.
In the synthesis process, L(-)-ALPHA-AMINO-EPSILON-CAPROLACTAM introduces the caprolactam moiety, which is crucial for the formation of the bengamide structure. This allows researchers to create novel bengamide analogs with potential therapeutic applications, expanding the scope of drug discovery and development in the pharmaceutical industry.

InChI:InChI=1/C6H12N2O.ClH/c7-5-3-1-2-4-8-6(5)9;/h5H,1-4,7H2,(H,8,9);1H/t5-;/m0./s1

Upstream product

• 657-27-2 L-Lysine hydrochloride 
• 56-87-1 L-lysine 
• 6804-88-2 α-nitrocaprolactam 
• 26081-03-8 (-)-3-aminocaprolactam hydrochloride 
• 13515-95-2 lysine methyl ester dihydrochloride 

Downstream Products

• 107885-67-6 (S)-3-aminohexahydro-2-azepine 
• 103478-12-2 (3S)-3-benzyloxycarbonylamino-2-perhydroazepinone 
• 334620-18-7 4-{(3S)-aminoazepin-1-yl}benzonitrile 
• 334620-20-1 4-[(S)-3-(Pyrimidin-2-ylamino)-azepan-1-yl]-benzonitrile 
• 334620-22-3 4-{(3S)-(pyrimidin-2-ylamino)azepin-1-yl}benzoic acid 
• 334620-24-5 (S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid tert-butyl ester 
• 7622-29-9 N^ε-methyllysine hydrochloride 
• 135607-26-0 (S)-hexahydro-1-methyl-3-tritylamino-2H-azepin-2-one 
• 1240399-62-5 Z-Ala-L-ACL 
• 449797-38-0 Z-Gly-L-ACL 
• 76944-95-1 tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate 
• 26081-03-8 3-Amino-azepan-2-one; hydrochloride 
• 70394-23-9 α-dimethylamino-ε-caprolactam 
• 105-60-2 caprolactam 

Relevant academic research and scientific papers

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

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.

Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids

(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.

SYNTHESIS OF CAPROLACTAM FROM LYSINE

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.

ANTI-INFLAMMATORY AGENTS

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.