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

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

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

Molecular Weight:: 115.09

MDL Number:: MFCD03411276

MOL File:: 2224-52-4.mol

Last updated:2023-10-25 12:39:57

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

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

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H332-H335
Precautionary statements	P261-P280-P305+P351+P338
HS Code	2934999090

(S)-4-Methyl-2,5-oxazolidonedione price More Price(12)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
TRC	C177720	N-CarboxyalanineAnhydride	2224-52-4	250mg	$115	2021-12-16	Buy
Apolloscientific	OR480799	(4S)-4-Methyloxazolidine-2,5-dione	2224-52-4	5g	$405	2021-12-16	Buy
American Custom Chemicals Corporation	AAA0000693	(S)-4-METHYL-2,5-OXAZOLIDINEDIONE 95.00%	2224-52-4	0.25G	$489	2021-12-16	Buy
American Custom Chemicals Corporation	AAA0000693	(S)-4-METHYL-2,5-OXAZOLIDINEDIONE 95.00%	2224-52-4	50G	$2500.69	2021-12-16	Buy
Ambeed	A399797	(S)-4-Methyloxazolidine-2,5-dione 95%	2224-52-4	100g	$910	2021-12-16	Buy

Product number	Packaging	Price	Buy
C177720	250mg	$115	Buy
OR480799	5g	$405	Buy
AAA0000693	0.25G	$489	Buy
AAA0000693	50G	$2500.69	Buy
A399797	100g	$910	Buy

(S)-4-Methyl-2,5-oxazolidonedione Chemical Properties,Uses,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 synthesis

Synthesis of (S)-4-Methyl-2,5-oxazolidonedione from L-Alanine and Triphosgene

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

Raw materials

Di-tert-butyl Tricarbonate N-(tert-Butoxycarbonyl)-L-alanine L-Alanine, N-(methoxycarbonyl)- (9CI) N-Carbobenzyloxy-L-alanine L-Alanine

Triphosgene Chloroform Diphosgene

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Preparation Products

L-Alanyl-L-proline

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

Global( 137)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Sichuan HongRi Pharma-Tech Co.,Ltd	+86-028-64841719 +8618980456393	daisy@enlaibio.com	China	1369	58
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15928	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	fandachem@gmail.com	China	9348	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Sichuan Jiaying Lai Technology Co.,LTD	18716376478	ycling@enlaibio.com	CHINA	302	58
Changzhou Carman Chemical Co., Ltd.	15061933924		CHINA	514	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
Alchem Pharmtech,Inc.	8485655694	sales@alchempharmtech.com	United States	63711	58

Supplier	Advantage
Sichuan HongRi Pharma-Tech Co.,Ltd	58
Shanghai Daken Advanced Materials Co.,Ltd	58
Henan Tianfu Chemical Co.,Ltd.	55
Hangzhou FandaChem Co.,Ltd.	55
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
Sichuan Jiaying Lai Technology Co.,LTD	58
Changzhou Carman Chemical Co., Ltd.	58
Chongqing Chemdad Co., Ltd	58
Alchem Pharmtech,Inc.	58

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-04-26	L-Ala-NCA 2224-52-4	US $0.00-0.00 / kg	1kg	98%	1T+	Sichuan HongRi Pharma-Tech Co.,Ltd
2022-01-27	(S)-4-methyloxazolidine-2,5-dione 2224-52-4	US $0.00 / KG	1KG	97.7%	100 tons	Honest Joy Holdings Limited
2020-01-06	L-Ala-NCA 2224-52-4	US $1.00 / g	10g	98%	100kg	Sichuan Jiaying Lai Technology Co.,LTD

L-Ala-NCA
2224-52-4
US $0.00-0.00 / kg
98%
Sichuan HongRi Pharma-Tech Co.,Ltd

(S)-4-methyloxazolidine-2,5-dione
2224-52-4
US $0.00 / KG
97.7%
Honest Joy Holdings Limited

L-Ala-NCA
2224-52-4
US $1.00 / g
98%
Sichuan Jiaying Lai Technology Co.,LTD

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

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(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 2,5-Oxazolidinedione,4-Methyl-, (4S)- (4S)-4-Methyloxazolidine-2,5-dione L-Alanine NC L-ALA-NCA(2224-52-4) (S)-4-METHYL-OXAZOLIDINE-2,5-DIONE L-Alanine N-Carbxy anhydride ALA-NCA L-Ala-NCA 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