ChemicalBook > CAS DataBase List > (S)-4-Methyl-2,5-oxazolidonedione

(S)-4-Methyl-2,5-oxazolidonedione

Product Name: (S)-4-Methyl-2,5-oxazolidonedione
CAS No.: 2224-52-4
Chemical Name: (S)-4-Methyl-2,5-oxazolidonedione
Synonyms: ALA-NCA;L-Ala-NCA;L-Alanine N-Carbxy anhydride;(S)-4-METHYL-OXAZOLIDINE-2,5-DIONE;H-ALA-NCA;H-L-Ala-NCA;Alanine, NCA;L-Alanine NC;L-ALA-NCA(2224-52-4);Creatinine Impurity 3
CBNumber: CB7180875
Molecular Formula: C4H5NO3
Formula Weight: 115.09
MOL File: 2224-52-4.mol

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(S)-4-Methyl-2,5-oxazolidonedione Property

Melting point:: 92℃
alpha: +5.13°(25/D,c=6.4,dioxane)
Density: 1.296
storage temp.: Inert atmosphere,Store in freezer, under -20°C
solubility: DMSO (Very Slightly, Heated)
form: Solid
pka: 9.38±0.40(Predicted)
color: White to Off-White
optical activity: 5.40°(C=0.01g/mL, DCM, 20°C, 589nm)
InChI: InChI=1S/C4H5NO3/c1-2-3(6)8-4(7)5-2/h2H,1H3,(H,5,7)/t2-/m0/s1
InChIKey: DTETYCNJKAUROO-REOHCLBHSA-N
SMILES: O1C(=O)[C@H](C)NC1=O

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Safety

HS Code: 2934999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: C177720
Product name: N-CarboxyalanineAnhydride
Packaging: 250mg
Price: $115
Updated: 2021/12/16

Apolloscientific

Product number: OR480799
Product name: (4S)-4-Methyloxazolidine-2,5-dione
Packaging: 5g
Price: $405
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: AAA0000693
Product name: (S)-4-METHYL-2,5-OXAZOLIDINEDIONE
Purity: 95.00%
Packaging: 0.25G
Price: $489
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: AAA0000693
Product name: (S)-4-METHYL-2,5-OXAZOLIDINEDIONE
Purity: 95.00%
Packaging: 50G
Price: $2500.69
Updated: 2021/12/16

Ambeed

Product number: A399797
Product name: (S)-4-Methyloxazolidine-2,5-dione
Purity: 95%
Packaging: 100g
Price: $910
Updated: 2021/12/16

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(S)-4-Methyl-2,5-oxazolidonedione Chemical Properties,Usage,Production

Description

(S)-4-Methyl-2,5-oxazolidonedione is also known as N-Carboxy anhydrides. The Fuchs-Farthing method, reported in 1922, was the only practical method for preparing (S)-4-Methyl-2,5-oxazolidonedione[1]. N-Carboxy anhydrides (NCAs) are important as α-amino acid building blocks for the synthesis of oligopeptides and nonpeptide compounds, and for the synthesis of polypeptides[2]. The polymerization of NCAs is the main process for the preparation of polypeptides, and its purity and side chains can significantly affect the synthesized polypeptides. NCAs polymerizations have been initiated using many different nucleophiles and bases, the most common being primary amines and alkoxide anions[3].

Uses

(S)-4-Methyl-2,5-oxazolidonedione is composed of oxazolidine ring and 2,5-dione ring. It exhibits chirality, meaning it exists as two non-superimposable mirror image forms. Therefore, it can be used as an organic reagent for the synthesis of enantiomeric pure substances. (S)-4-Methyl-2,5-oxazolidonedione is a reagent used in the synthesis of poly(γ-benzyl-L-glutamate) and its block polypeptides with alanine, leucine and phenylalanine.

Production Methods

L-alanine (20.0 g, 0.224 mol) and triphosgene (53.4 g, 0.180 mol) were suspended in 400.0 mL of dry THF bubbled with nitrogen flux in a flame-dried three-neck flask. The mixture was stirred at 60 °C for 2 h before further bubbling with nitrogen flux for 30 min. After that, the solution was precipitated in 1000.0 mL of n-hexane and stored at -20 °C. The supernatant was removed, and the residues were collected and dissolved in 200.0 mL of ethyl acetate, before two washings with 100.0mL of ice-cold water and one washing with 100.0 mL of 0.5% NaHCO3 ice-cold aqueous solution. The organic phase was then dried over anhydrous MgSO4 and evaporated to obtain 15.5 g of L-Ala NCA ((S)-4-Methyl-2,5-oxazolidonedione). The yield of L-Ala NCA was 77.5%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2200, 1985 DOI: 10.1021/jo00212a042

References

[1] Otake Y, et al. Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor. Angewandte Chemie International Edition, 2018; 57: 11389-11393.
[2] Sch?fer G, et al. Synthesis of Sterically Hindered N-Acylated Amino Acids from N-Carboxyanhydrides. Organic Letters, 2014; 16: 1526–1529.
[3] Imanishi Y, et al. Polymerization of α-amino acid N-carboxyanhydride in the presence of preformed poly(α-amino acid) - from chain effect to stereoselective polymerization. Pure and Applied Chemistry, 1981; 53.

(S)-4-Methyl-2,5-oxazolidonedione Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (S)-4-Methyl-2,5-oxazolidonedione manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: (S)-4-Methyloxazolidine-2,5-dione 2224-52-4
Price: US $2.00-5.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2025-06-24

Sichuan HongRi Pharma-Tech Co.,Ltd

Product: L-Ala-NCA 2224-52-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1T+
Release date: 2023-09-26

Honest Joy Holdings Limited

Product: (S)-4-methyloxazolidine-2,5-dione 2224-52-4
Price: US $0.00/KG
Min. Order: 1KG
Purity: 97.7%
Supply Ability: 100 tons
Release date: 2022-01-26

2224-52-4, (S)-4-Methyl-2,5-oxazolidonedioneRelated Search:

FMOC-ALA-N-CARBOXYANHYDRIDE Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate 3-(3,5-DICHLOROPHENYL)-5-ETHENYL-5-METHYL-2,4-OXAZOLIDINEDIONE,(+or-)-3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedion 5-METHYL-2,4-OXAZOLIDINEDIONE FMOC-GLU(OTBU)-N-CARBOXYANHYDRIDE BOC-O-BENZYL-L-SERINE N-CARBOXY ANHYDRIDE NALPHA-9-Fluorenylmethoxycarbonyl-L-leucine N-carboxylic anhydride BOC-ASP(OBZL)-N-CARBOXYANHYDRIDE BOC-L-ALANINE-NCA N-α-Fmoc-N-γ-trityl-L-asparagine N-carboxyanhydride BOC-O-BENZYL-L-THREONINE N-CARBOXY ANHYDRIDE FMOC-L-VALINE N-CARBOXY ANHYDRIDE N-α-Boc-N-ε-Z-L-lysine N-carboxyanhydride Fmoc-O-tert·butyl-L-threonineN-carboxyanhydride FMOC-ILE-N-CARBOXYANHYDRIDE BOC-TRYPTOPHAN NCA N-tert-Butoxycarbonyl-L-leucine N-carboxylic anhydride BOC-ILE-N-CARBOXYANHYDRIDE

(S)-4-METHYL-OXAZOLIDINE-2,5-DIONE

(S)-4-METHYL-2,5-OXAZOLIDINEDIONE

(S)-4-Methyl-2,5-oxazolidonedione

H-ALA-NCA

Alanine, NCA

N-Carboxy-L-alanine anhydride

4-methyl-1,3-oxazolidine-2,5-dione

4-methyloxazolidine-2,5-quinone

N-Carboxyalanine Anhydride

(4S)-4-Methyl-1,3-oxazolidine-2,5-dione

L-Alanine N-Carbxy anhydride

2,5-Oxazolidinedione,4-Methyl-, (4S)-

(4S)-4-Methyloxazolidine-2,5-dione

ALA-NCA

L-Ala-NCA

L-Alanine NC

L-ALA-NCA(2224-52-4)

L-Ala-N-Carboxyanhydride

Alanine N-carboxyanhydride

Creatinine Impurity 3

L-alanine-n-carboxylic intracyclic anhydride

H-L-Ala-NCA

Sodium Phenylbutyrate Impurity 4

2224-52-4

AMINOACIDS DERIVATIVES