474534-78-6

Basic information

• Product Name: (S)-N-benzyl-2-amino-3-methoxypropionamide
• Synonyms: (S)-N-benzyl-2-amino-3-methoxypropionamide
• CAS NO: 474534-78-6
• Molecular Weight: 208.26
• Mol File: 474534-78-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyl-2-amino-3-methoxypropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyl-2-amino-3-methoxypropionamide(474534-78-6)
• EPA Substance Registry System: (S)-N-benzyl-2-amino-3-methoxypropionamide(474534-78-6)

Safety Data

• Hazardous Substances Data: 474534-78-6(Hazardous Substances Data)

Upstream product

• 19794-53-7 3-methoxy-2-aminopropionic acid 
• 100-46-9 benzylamine 
• 790692-10-3 (S)-N-benzyl-1-tritylaziridine-2-carboxamide 
• 86118-11-8 D-o-methylserine 
• 1567820-77-2 (S)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl 4-toluenesulfonate 
• 1567820-75-0 (S)-N-benzyl-2-hydroxy-3-methoxypropanamide 
• 1567820-72-7 (S)-3-(benzylamino)-2-hydroxy-3-oxopropyl 4-toluenesulfonate 
• 205122-64-1 (S)-N-benzyl 2,3-dihydroxypropionamide 
• 13304-62-6 N-benzylacrylamide 
• 180060-98-4 (S)-N-benzyl-2-N-(benzyloxycarbonyl)amino-3-hydroxypropionamide 
• 474534-77-5 (S)-N-benzyl-2-N-(benzyloxycarbonyl)amino-3-methoxypropionamide 

Downstream Products

• 175481-36-4 lacosamide 
• 1609102-50-2 C₃₁H₄₄N₂O₃ 
• 262845-82-9 N-Benzyl-2-Amino-3-Methoxypropionamide 
• 1609160-80-6 (R)-N-benzyl-2-amino-3-methoxypropanamide N-formyl-L-leucine salt 
• 175481-36-4 (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide 

Relevant articles and documents

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.

Direct amidation of unprotected amino acids using B(OCH2CF3)3

A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of α-amino acids with a range of amines in cyclopentyl methyl ether. The method can be applied to the synthesis of medicinally relevant compounds, and can be scaled up to obtain gram quantities of products.

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.