55686-06-1

Basic information

• Product Name: 5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-
• CAS NO: 55686-06-1
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• Mol File: 55686-06-1.mol

Chemical Properties

• CAS DataBase Reference: 5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-(55686-06-1)
• EPA Substance Registry System: 5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-(55686-06-1)

Safety Data

• Hazardous Substances Data: 55686-06-1(Hazardous Substances Data)

Upstream product

• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 74-88-4 methyl iodide 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 100-39-0 benzyl bromide 
• 2566-22-5 DL-N-benzoylphenylalanine 
• 2198-64-3 N-Benzoylalanine 
• 4218-62-6 benzyl diphenyl phosphate 
• 884-90-2 benzyl diethyl phosphate 
• 1369423-47-1 diphenyl 4-fluorobenzyl phosphate 
• 459-56-3 4-fluorobenzylic alcohol 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 169566-66-9 N²-<(R)-N²-benzoyl-2-methyl-phenylalanyl>-(S)-phenylalanine cyclohexylamide 
• 1132-26-9 2-methyl-3-phenylalanine 
• 55686-06-1 (S)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one 
• 325462-14-4 [(4-benzyl-4-methyl-2-phenyl-5(4H)-oxazolone)PtCl₂(P(nBu)3)] 
• 325462-15-5 [(4-benzyl-4-methyl-2-phenyl-5(4H)-oxazolone)PtCl₂(PEt₃)] 
• 325462-16-6 [(4-benzyl-4-methyl-2-phenyl-5(4H)-oxazolone)PdCl₂(PEt₃)] 
• 169738-76-5 (R)-methyl 2-benzamido-2-methyl-3-phenylpropanoate 

Relevant articles and documents

Palladium-catalyzed asymmetric benzylation of azlactones

Asymmetric benzylation of prochiral azlactone nucleophiles enables the catalytic introduction of a benzyl group towards the synthesis of α,α-disubstituted amino acids. Herein, we report an enantioselective palladium-catalyzed process using chiral bis(diphenylphosphinobenzoyl)diamine (dppba) ligands. Naphthalene- and heterocycle-based methyl carbonates react with a number of azlactones derived from both natural and unnatural amino acids. Monocyclic benzylic electrophiles, for which the barrier to ionization is higher, must employ a phosphate leaving group in order to react. Reaction conditions for electron-rich and -neutral benzylic electrophiles have been developed, and the scope of the reaction has been explored with respect to both reaction partners. The high levels of asymmetric induction, as well as the reactivity pattern of the electrophiles, suggest an η3-benzyl intermediate that arises through two distinct pathways. Attack on benzyl: Palladium-catalyzed asymmetric benzylation methodology is demonstrated on prochiral azlactone nucleophiles. The use of naphthyl, heterocyclic, and monocyclic benzylic electrophiles demonstrates the wide reaction scope (see scheme; Cp=cyclopentadienyl). The benzylation products are readily converted into enantioenriched α,α-disubstituted amino acids.

BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids

Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free α,α-dialkyl-α-amino acids, were obtained in high yields (up to 99%

Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones

Palladium-catalyzed asymmetric benzylation has been demonstrated with azlactones as prochiral nucleophiles in the presence of chiral bisphosphine ligands. Benzylic electrophiles are utilized under two sets of reaction conditions to construct a new tetrasubstituted stereocenter. Electron density of the phenyl ring dictates the reaction conditions, including the leaving group. The reported methodology represents a novel asymmetric carbon-carbon bond formation in an amino acid precursor.

A reinvestigation of the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones ('azlactones'): A general entry into highly functionalized α,α-disubstituted α-amino acids

Novel, more reliable and general reaction conditions for the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones (= 4-monosubstituted 2-phenyl-azlactones) rac-2 to 4,4-disubstituted 2-phenyloxazol-5(4H)-ones rac-1 were found. Thus, a whole range of highly functionalized rac-1 were prepared in medium-to-good overall yields (40-90%). Azlactones rac-1 are ideal precursors for the synthesis of optically pure α,α-disubstituted (R)- and (S)-α-amino acids.

SYNTHESIS OF α-SUBSTITUTED α-AMINO ACIDS BY THE ALKYLATION OF 5-OXAZOLINONE DERIVATIVES

Methods have been developed for the alkylation of 5-oxazolinone derivatives in DMF in the presence of K2CO3, KOH, or diisopropylethylamine and a phase transfer catalyst as well as for the preparation of α-methylphenylalanine, α-methylalanine, α-methylalanine, and the methyl ester of N-benzoyl-α-methylalanine.Increasing the initial concentration of the starting 5-oxazolinone in the reaction mixture leads to a sharp drop in the yield of reaction products due to side condensation reactions.The reaction of 2-phenyl-4-benzyl-5-oxazolinonewith ethyl iodide gave a dimer, mamely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.