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

• 63-91-2 L-phenylalanine 
• 74-89-5 methylamine 
• 3081-24-1 H-Phe-OEt 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1161-13-3 N-Cbz-L-Phe 
• 35661-40-6 N-Fmoc L-Phe 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 214344-15-7 (L)-Trt-Phe-F 
• 47672-25-3 N-trityl-L-phenylalanine 
• 87877-11-0 Phe-Chlor 
• 203446-11-1 Trt-(L)-Phe-NHMe 

Downstream Products

• 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 
• 60079-69-8 N-(benzyloxycarbonyl)-L-leucyl-L-phenylalanine methylamide 
• 264887-78-7 N-benzyloxycarbonyl-L-valyl-L-phenylalanine methylamide 
• 474974-00-0 (2R,3S)-2-Isobutyl-3-(2-oxo-oxazolidine-3-carbonyl)-hex-5-enoic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide 
• 415678-38-5 (2S,5S)-5-benzyl-3-methyl-2-phenylimidazolidin-4-one 
• 415678-38-5 (2R,5S)-5-benzyl-3-methyl-2-phenylimidazolidin-4-one 
• 111258-73-2 (S)-2-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 390766-89-9 C₁₅H₂₂N₂O 
• 911289-59-3 C₃₀H₂₉N₃O₄ 
• 911289-30-0 C₁₆H₁₇N₃O₄*ClH 
• 691847-46-8 (2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride 

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

Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols

Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide evidence for SCS as a key elementary step, identify the origins of competing reactions, and enable improvements in chemoselectivity by rational photocatalyst design.