140861-05-8

Basic information

• Product Name: DL-Phenylalanine, N-benzoyl-4-methyl-, methyl ester
• CAS NO: 140861-05-8
• Molecular Formula: C18H19NO3
• Molecular Weight: 297.354
• Mol File: 140861-05-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: DL-Phenylalanine, N-benzoyl-4-methyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Phenylalanine, N-benzoyl-4-methyl-, methyl ester(140861-05-8)
• EPA Substance Registry System: DL-Phenylalanine, N-benzoyl-4-methyl-, methyl ester(140861-05-8)

Safety Data

• Hazardous Substances Data: 140861-05-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 104-87-0 4-methyl-benzaldehyde 
• 495-69-2 Hippuric Acid 
• 106-42-3 para-xylene 
• 1205-08-9 methyl hippurate 
• 101649-82-5 N-benzoyl-2-bromoglycine methyl ester 
• 29875-07-8 (4-methylbenzyl)magnesium chloride 
• 57427-79-9 (Z)-4-(4-methylbenzylidene)-2-phenyloxazol-5(4H)-one 

Downstream Products

• 280747-78-6 N-bromo-N-tert-butyl-N^α-phthaloyl-p-methylphenylalaninamide 
• 280747-79-7 N-tert-butyl-N^α-phthaloyl-p-methylphenylalaninamide 
• 111210-65-2 2-(1,3-dioxoisoindolin-2-yl)-3-(p-tolyl)propanoic acid 
• 4599-47-7 p-methylphenylalanine 

Relevant articles and documents

Stereoselective Synthesis of 1,3-Diaminotruxillic Acid Derivatives: An Advantageous Combination of C-H-ortho-Palladation and On-Flow [2+2]-Photocycloaddition in Microreactors

The stereoselective synthesis of ε-isomers of dimethyl esters of 1,3-diaminotruxillic acid in three steps is reported. The first step is the ortho-palladation of (Z)-2-aryl-4-aryliden-5(4H)-oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho-C-H bond of the 4-arylidene ring in carboxylic acids. The second step is the [2+2]-photocycloaddition of the C-C exocyclic bonds of the oxazolone skeleton in 2 to afford the corresponding dinuclear ortho-palladated cyclobutanes 3. This key step was performed very efficiently by using LED light sources with different wavelengths (465, 525 or 625 nm) in flow microreactors. The final step involved the depalladation of 3 by hydrogenation in methanol to afford the ε-1,3-diaminotruxillic acid derivatives as single isomers.

Photochemical alkylation of glycine leading to phenylalanines

UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, benzophenone and substituted toluenes is shown to lead to selective alkylation at the α-position. Phenylalanines are isolated in yields of generally > 50% (based on recovered s

Synthesis of (S)-3,4-dihydroxyphenylalanine (L-DOPA) and unnatural α-amino acids via enzymatic resolution using alcalase

Enzymatic resolution has been used for the synthesis of L-DOPA with high optical purity.N-Acetyl-(R,S)-3,4-methylenedioxyphenylalanine methyl ester (2b) on enzymatic resolution by alcalase (Subtilisin Carlsberg) yields N-acetyl-(S)-3,4-methylenedioxyphenylalanine (3b) which upon acid treatment affords (S)-3,4-dihydroxyphenylalanine (L-DOPA) (4).Several optically active unnatural N-acetylated and N-benzoylated α-amino acids have been prepared by similar enzymatic resolution.