2185-00-4

Basic information

• Product Name: 2,5-OXAZOLIDINEDIONE
• Synonyms: N-Carboxyglycine anhydride;GLY-NCA;L-Gly-NCA;2,5-OXAZOLIDINEDIONE;GLYCINE-N-CARBOXYANHYDRIDE;oxazolidine-2,5-dione;1,3-oxazolidine-2,5-dione
• CAS NO: 2185-00-4
• Molecular Formula: C₃H₃NO₃
• Molecular Weight: 101.06
• EINECS: 218-570-6
• Product Categories: pharmacetical;Anhydride Monomers;Monomers;Polymer Science
• Mol File: 2185-00-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 120 °C (dec.)(lit.)
• Appearance: /
• Density: 1.469 g/cm³
• Refractive Index: 1.465
• Storage Temp.: -15°C
• PKA: 9.32±0.20(Predicted)
• CAS DataBase Reference: 2,5-OXAZOLIDINEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-OXAZOLIDINEDIONE(2185-00-4)
• EPA Substance Registry System: 2,5-OXAZOLIDINEDIONE(2185-00-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2185-00-4(Hazardous Substances Data)

Usage

Preparation

Different sources of media describe the Preparation of 2185-00-4 differently. You can refer to the following data:
1. Into a suspension of finely ground glycine (15 g) in dry dioxane (750 mL), phosgene was introduced in a fine stream at 45–50 °C with efficient agitation. A clear solution was obtained after 5 h. This solution was filtered to remove unreacted glycine (1.7 g), and the dioxane was then removed under reduced pressure at a temperature below 40 °C with protection from moisture. The residue was treated with dry diethyl ether (100 mL), and the crystals of 2,5-oxazolidinedione were collected by filtration and dried over P2O5 in a vacuum desiccator. The crude product so obtained, 16 g (89%), was recrystallized from ethyl acetate/petroleum ether to yield 14.3 g (77.2%) of pure material, which showed no melting point because of polymerization.
2. Phosgene was passed in a fine stream into a suspension of finely ground glycine (15 g) in dry dioxane (750 mL) at 45–50 ℃ with efficient agitation. A clear solution was obtained after 5 h. This solution was filtered to remove unreacted glycine (1.7 g), and the dioxane was then removed under reduced pressure at a temperature below 40 ℃ under exclusion of moisture. The residue was treated with dry diethyl ether (100 mL), and the crystals of 2,5-oxazolidinedione were collected by filtration and dried over P2O5 in a vacuum desiccator. The crude product thus obtained, 16 g (89%), was recrystallized from ethyl acetate/petroleum ether to yield 14.3 g (77.2%) of pure material, which showed no melting point because of polymerization.

InChI:InChI=1/C3H3NO3/c5-2-1-4-3(6)7-2/h1H2,(H,4,6)

Upstream product

• 1670-97-9 N-(methoxycarbonyl)glycine 
• 4596-51-4 N-(ethoxycarbonyl)glycine 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 67-66-3 chloroform 
• 56-40-6 glycine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 6000-44-8 sodium glycinate 
• 758-10-1 thioglycine 
• 144-55-8 sodium hydrogencarbonate 
• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 15050-24-5 N-(benzyloxycarbonyl)glycyl chloride 
• 75-44-5 phosgene 

Downstream Products

• 1963-21-9 L-glycyl-L-valine 
• 3321-03-7 Gly-Phe-OH 
• 16817-90-6 2-amino-N-cyclohexylacetamide 
• 33557-91-4 3-Cyclohexylureidoessigsaeure 
• 39796-52-6 N-benzyl-2-aminoacetamide 
• 34582-41-7 2-[(benzylcarbamoyl)amino]acetic acid 
• 23961-18-4 N-(4-glycylamino-benzoyl)-L-glutamic acid 
• 7496-53-9 4-glycylamino-benzoic acid 
• 90557-83-8 N-glycyl-anthranilic acid 
• 38219-44-2 4-glycylamino-benzoic acid ethyl ester 
• 34582-49-5 5-p-Tolyl-hydantoinsaeure 
• 40331-72-4 3-(2-nitro-phenylsulfanyl)-oxazolidine-2,5-dione 
• 4746-64-9 2-aminoacetyl chloride 
• 758-10-1 thioglycine 

Relevant articles and documents

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METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE

PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor

Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.