23224-65-9

Basic information

• Product Name: 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (S)-
• CAS NO: 23224-65-9
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.223
• Mol File: 23224-65-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (S)-(23224-65-9)
• EPA Substance Registry System: 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (S)-(23224-65-9)

Safety Data

• Hazardous Substances Data: 23224-65-9(Hazardous Substances Data)

Usage

Chemical class

2,5-oxazolidinediones

Chirality

(S) configuration

Structure

2,5-oxazolidinedione ring and an acetyloxyphenylmethyl group

Usage

potential building block for the synthesis of various compounds in the pharmaceutical industry

Applications

drug development, medicinal chemistry, and research and development for new therapeutic agents.

Upstream product

• 75-44-5 phosgene 
• 6636-22-2 O-acetyl-L-tyrosine 
• 503-38-8 trichloromethyl chloroformate 
• 3415-08-5 L-tyrosine N-carboxyanhydride 
• 75-36-5 acetyl chloride 
• 51514-13-7 O-acetyl-N-benzyloxycarbonyl L-tyrosine 
• 60-18-4 L-tyrosine 

Downstream Products

• 73044-67-4 (S)-4-(4-acetoxy-benzyl)-3-xanthen-9-yl-oxazolidine-2,5-dione 
• 71667-73-7 L-alanyl=>L-tyrosyl=>glycine 
• 673-08-5 YG 
• 21778-69-8 tyrosylglycylglycine 
• 1050-28-8 (S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid 

Relevant articles and documents

Large-scale synthesis of α-amino acid-N-carboxyanhydrides

Hetero- and homopolymers prepared from α-amino acid-N-carboxyanhydrides (NCAs) monomers are widely useful products. The preparation of pure NCA monomers has been extensively studied in the past. Purification methods including repeated crystallizations, extraction, and flash column chromatography have been devised. However, these methods are not easily amendable to large-scale NCA preparations. This article describes the synthesis of numerous highly purified NCAs on a >100 g scale using a simple filtration step through diatomaceous earth (celite). The resulting NCAs provided polyethylene glycol (PEG)–amino acid triblock polymers devoid of low-molecular-weight by-products that were routinely observed when unfiltered batches of NCAs were used. Also disclosed is the preparation of NCAs at ambient temperature. Traditionally, NCA reactions using a phosgene source are heated. This study shows these reactions can be driven by the slight exotherm that forms upon reagent mixing. This eliminates the need for an external heating source, simplifying large-scale reactions.