35373-92-3

Basic information

• Product Name: L-Phenylalanine methylamide
• Synonyms: L-Phenylalanine methylamide;L-PHENYLALANINE N-METHYLAMIDE;S-α-aMino-N-Methyl-BenzenepropanaMide;(S)-2-Amino-N-methyl-3-phenylpropanamide,98%e.e.
• CAS NO: 35373-92-3
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.23
• Mol File: 35373-92-3.mol
• Article Data: 46

Chemical Properties

• Melting Point: 58-60 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 379.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.078±0.06 g/cm3(Predicted)
• PKA: 15.58±0.46(Predicted)
• CAS DataBase Reference: L-Phenylalanine methylamide(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine methylamide(35373-92-3)
• EPA Substance Registry System: L-Phenylalanine methylamide(35373-92-3)

Safety Data

• Hazardous Substances Data: 35373-92-3(Hazardous Substances Data)

Upstream product

• 15368-72-6 (S)-N-Benzyloxycarbonyl-phenylalanine-N'-methylamide 
• 109522-21-6 N-(t-butoxycarbonyl)-L-phenylalanine methylamide 
• 120346-32-9 (3S,4R)-1-methyl-4-phenyl-3-[(4S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-azetidin-2-one 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 124-40-3 dimethyl amine 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 63-91-2 L-phenylalanine 
• 74-89-5 methylamine 
• 3081-24-1 H-Phe-OEt 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 203446-11-1 Trt-(L)-Phe-NHMe 
• 87877-11-0 Phe-Chlor 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 143348-11-2 N-(tert-butoxycarbonyl)isoleucinylphenylalanine methylamide 
• 63509-00-2 Ac-Pro-L-Phe-NHMe 
• 120125-06-6 Boc-D-Arg(NO₂)-Phe-NHCH₃ 
• 128899-92-3 2-amino-1-N-methylamino-3-phenylpropane 
• 129155-77-7 (S)-5-Benzyl-2-(4-methoxy-phenyl)-3-methyl-imidazolidin-4-one 
• 67120-04-1 (S)-N-Methyl-3-phenyl-2-(3-phenyl-thioureido)-propionamide 
• 132278-63-8 (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one 

Relevant articles and documents

Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions

The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids

Both E- and Z-N′-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K+ and [18]crown-6 induces intramolecular migration of the alkeny

Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor

The β2-adrenergic receptor (β2AR), a G protein-coupled receptor, is an important therapeutic target. We recently described Cmpd-15, the first small molecule negative allosteric modulator (NAM) for the β2AR. Herein we report in details the design, synthesis and structure-activity relationships (SAR) of seven Cmpd-15 derivatives. Furthermore, we provide in a dose-response paradigm, the details of the effects of these derivatives in modulating agonist-induced β2AR activities (G-protein-mediated cAMP production and β-arrestin recruitment to the receptor) as well as the binding affinity of an orthosteric agonist in radio-ligand competition binding assay. Our results show that some modifications, including removal of the formamide group in the para-formamido phenylalanine region and bromine in the meta-bromobenzyl methylbenzamide region caused dramatic reduction in the functional activity of Cmpd-15. These SAR results provide valuable insights into the mechanism of action of the NAM Cmpd-15 as well as the basis for future development of more potent and selective modulators for the β2AR based on the chemical scaffold of Cmpd-15.