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;Alanine, NCA;L-Alanine NC;L-ALA-NCA(2224-52-4);Creatinine Impurity 3;L-Ala-N-Carboxyanhydride
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
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

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
Sichuan Jiaying Lai Technology Co.,LTD
Product
L-Ala-NCA 2224-52-4
Price
US $1.00/g
Min. Order
10g
Purity
98%
Supply Ability
100kg
Release date
2019-07-14

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


  • (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
  • Sodium Phenylbutyrate Impurity 4
  • L-alanine-n-carboxylic intracyclic anhydride
  • 2224-52-4
  • AMINOACIDS DERIVATIVES