52421-48-4

Basic information

• Product Name: DL-N-BENZOYL-2-BENZYLSERINE
• Synonyms: DL-N-BENZOYL-2-BENZYLSERINE;DL-2-BENZOYLAMINO-2-HYDROXYMETHYL-3-PHENYLPROPIONIC ACID
• CAS NO: 52421-48-4
• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.32
• Mol File: 52421-48-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 160-162 °C
• Boiling Point: 440.65°C (rough estimate)
• Flash Point: 314.8 ºC
• Appearance: white
• Density: 1.1441 (rough estimate)
• Vapor Pressure: 4.25E-15mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• CAS DataBase Reference: DL-N-BENZOYL-2-BENZYLSERINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-N-BENZOYL-2-BENZYLSERINE(52421-48-4)
• EPA Substance Registry System: DL-N-BENZOYL-2-BENZYLSERINE(52421-48-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 52421-48-4(Hazardous Substances Data)

Usage

General Description

DL-N-benzoyl-2-benzylserine is a chemical compound that belongs to the class of benzoyl amino acids. It is a derivative of benzoylserine, which is a naturally occurring amino acid found in proteins. DL-N-benzoyl-2-benzylserine is used in pharmaceutical research and development as a building block in the synthesis of various compounds. It has potential applications in the fields of medicinal chemistry and drug discovery, as well as in the study of biochemical pathways and processes. The compound may have potential therapeutic properties and could be of interest for further investigation in the development of new drugs.

InChI:InChI=1/C17H17NO4/c19-12-17(16(21)22,11-13-7-3-1-4-8-13)18-15(20)14-9-5-2-6-10-14/h1-10,19H,11-12H2,(H,18,20)(H,21,22)/p-1/t17-/m1/s1

Upstream product

• 51127-28-7 (RS)-5-benzoylamino-5-benzyl-4-oxo-1,3-dioxane 
• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 2566-22-5 DL-N-benzoylphenylalanine 

Downstream Products

• 185396-34-3 (S)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid 
• 185396-33-2 (R)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid 
• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 
• 161956-17-8 (R)-2-benzoylamino-2-methyl-3-phenylpropanoic acid 
• 185396-39-8 (S)-2-benzoylamino-2-benzyl-3-tosylpropanoic acid 
• 185396-37-6 (R)-2-amino-3-hydroxy-2-benzylpropionic acid 
• 185396-36-5 (S)-α-(hydroxymethyl)-D-phenylalanine 

Relevant articles and documents

Optical resolution by preferential crystallization of (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid and its use in synthesizing optically active 2-amino-2-methyl-3-phenylpropanoic acid.

To synthesize optically active 2-amino-2-methyl-3-phenylpropanoic acid (1), (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid [(RS)-2] was first optically resolved using cinchonidine as a resolving agent to yield optically pure (S)- and (R)-2 in yields of about 70%, based on half of the starting amount of (RS)-2. Next, the racemic structure of (RS)-2 was examined based on melting point, solubility, IR spectrum, and binary and ternary phase diagrams, with the aim of optical resolution by preferential crystallization of (RS)-2. Results indicated that the (RS)-2 exists as a conglomerate at room temperature, although it forms a racemic compound at the melting point. The optical resolution by preferential crystallization yielded (S)- and (R)-2 with optical purities of about 90%, which were fully purified by recrystallization. After O-tosylation of (S)- and (R)-2, reduction by zinc powder and sodium iodide gave (R)- and (S)-1, respectively.