7352-07-0

Basic information

• Product Name: N-Benzoyl-L-phenylglycine
• Synonyms: N-Benzoyl-L-phenylglycine;(R)-(Benzoylamino)phenylacetic acid;(R)-2-Phenyl-2-(benzoylamino)acetic acid;[R,(-)]-2-(Benzoylamino)-2-phenylacetic acid;(+)-α-Phenylhippuric acid;(S)-(Benzoylamino)phenylacetic acid;[S,(+)]-2-(Benzoylamino)-2-phenylacetic acid
• CAS NO: 7352-07-0
• Molecular Formula: C₁₅H₁₃NO₃
• Molecular Weight: 255.26862
• Mol File: 7352-07-0.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Benzoyl-L-phenylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-L-phenylglycine(7352-07-0)
• EPA Substance Registry System: N-Benzoyl-L-phenylglycine(7352-07-0)

Safety Data

• Hazardous Substances Data: 7352-07-0(Hazardous Substances Data)

Upstream product

• 28687-81-2 2,4-diphenyl-4H-oxazol-5-one 
• 2935-35-5 (S)-2-phenylglycine 
• 98-88-4 benzoyl chloride 
• 188772-84-1 (S)-N-[(furan-2-yl)(phenyl)methyl]benzamide 
• 29670-63-1 N-benzoyl-2-phenylglycine 
• 188772-74-9 (S)-(furan-2-yl)(phenyl)methanamine 
• 219802-35-4 (S)-2-[((S)-Furan-2-yl-phenyl-methyl)-amino]-3-methyl-butan-1-ol 
• 688362-39-2 N-[(1R)-1-phenylprop-2-en-1-yl]benzamide 
• 65-85-0 benzoic acid 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 6175-45-7 2,2-diethoxyacetophenone 
• 163010-72-8 N-benzoyl-(S)-phenylglycinal 

Downstream Products

• 117370-53-3 Bz-Phg-Val-OMe 
• 56023-84-8 (2S,3S)-1-Acetyl-2,5-diphenyl-2,3-dihydro-1H-pyrrole-3-carbonitrile 
• 56023-83-7 (2S,3S)-1-Acetyl-2,5-diphenyl-2,3-dihydro-1H-pyrrole-3-carboxylic acid methyl ester 
• 90421-35-5 2-(Acetylamino-phenyl-methyl)-2-methyl-4-oxo-4-phenyl-butyric acid methyl ester 
• 153524-49-3 1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 614-28-8 N-benzoylbenzamide 
• 135357-90-3 (2R)-N-benzyl-2-amino-2-phenyl-1-ethanol 
• 153433-79-5 2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester 
• 153433-82-0 anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester 
• 153433-80-8 ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 90421-34-4 N-(2-Cyano-4-oxo-1,4-diphenyl-butyl)-acetamide 
• 90421-33-3 2-(Acetylamino-phenyl-methyl)-4-oxo-4-phenyl-butyric acid methyl ester 

Relevant articles and documents

Direct asymmetric reductive amination of α-keto acetals: A platform for synthesizing diverse α-functionalized amines

We report an efficient and straightforward method to synthesize enantio-enriched N-unprotected α-amino acetals via ruthenium-catalyzed direct asymmetric reductive amination. The α-amino acetal products are versatile and valuable platform molecules that can be converted to the corresponding α-amino acids, amino alcohols, and other derivatives by convenient transformations.

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.

Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines

The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.