24601-74-9

Basic information

• Product Name: (S)-4-ISOPROPYLOXAZOLIDINE-2,5-DIONE
• Synonyms: (S)-4-ISOPROPYLOXAZOLIDINE-2,5-DIONE;L-Valine-N-carboxyanhydride;H-Val-NCA;(4S)-4-(1-Methylethyl)-2,5-oxazolidinedione;L-4-Isopropyl-2,5-oxazolidinedione;N-Carboxy-L-valine Anhydride;Valine N-Carboxyanhydride;2,5-Oxazolidinedione, 4-(1-methylethyl)-, (4S)-
• CAS NO: 24601-74-9
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14
• EINECS: 221-692-2
• Product Categories: AMINOACIDS DERIVATIVES;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 24601-74-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 70-71°C
• Appearance: /
• Density: 1.184 g/cm³
• Refractive Index: 1.457
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 9.26±0.40(Predicted)
• CAS DataBase Reference: (S)-4-ISOPROPYLOXAZOLIDINE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-ISOPROPYLOXAZOLIDINE-2,5-DIONE(24601-74-9)
• EPA Substance Registry System: (S)-4-ISOPROPYLOXAZOLIDINE-2,5-DIONE(24601-74-9)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 24601-74-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

L-Valine N-Carboxyanhydride (cas# 24601-74-9) is a compound useful in organic synthesis.

Preparation

To a stirred suspension of l-valine (46.8 g, 0.4 mol) in dry THF (400 mL) was slowly added a solution of phosgene (0.8 mol)in toluene (stock solution ca. 5 m). In the closed vessel (Author’s remark: It is better to use a reflux condenser cooled to at least -15 ℃ or a dry-ice reflux condenser under ambient pressure), the mixture was stirred at 45 ℃ for 7 h in order to obtain a clear solution. The solvent was then evaporated in vacuo at room temperature. The residue was redissolved in dry THF and this solution was concentrated to dryness. The crystalline residue was dried over CaCl2 in vacuo; yield 57.0 g (quantitative).

InChI:InChI=1/C6H9NO3/c1-3(2)4-5(8)10-6(9)7-4/h3-4H,1-2H3,(H,7,9)/t4-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 516-06-3 D,L-valine 
• 26081-00-5 N-carbamoyl-valine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 15984-93-7 valine, N-trimethylsilyl-, trimethylsilyl ester 
• 1149-26-4 N-benzyloxycarbonylvaline 
• 111421-95-5 N-ethoxycarbonyl-DL-valine 
• 111398-44-8 (2R)-2-(methoxycarbonyl amino)-3-methylbutanoic acid 

Downstream Products

• 55721-76-1 valine phenethylamide 
• 13474-14-1 valinamide 
• 40331-73-5 4-isopropyl-3-(2-nitro-phenylsulfanyl)-oxazolidine-2,5-dione 
• 72-18-4 L-valine 
• 686-43-1 valylglycine 
• 3918-94-3 Val-Val 
• 462-60-2 N-carbamoylglycine 
• 633-90-9 cytidine 2',3'-cyclic monophosphate 
• 154674-67-6 methyl (R)-(N-benzyloxycarbonyl)valinate 
• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 394210-42-5 4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester 
• 634-01-5 adenosine 2',3'-cyclic monophosphate 
• 16944-60-8 (2S)-isopropylpiperazine-3,6-dione 

Relevant articles and documents

Stereospecific hydrogenations. IV. Palladium-on-poly-S-valine and palladium-on-poly-S-leucine.

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ANTIMICROBIAL COMPOSITION COMBINATIONS COMPRISING STAR SHAPED PEPTIDE POLYMERS

This invention relates to compositions including antibacterial compounds. The invention also relates to the use of the compositions in methods of treating bacterial infections. In one aspect the present invention also provides a method of increasing the susceptibility of bacteria to the anti-bacterial activity of a compound, the method comprising contacting the bacteria with a star shaped peptide polymer of the invention, thereby increasing the susceptibility of the bacteria to the anti-bacterial activity of the compound. Preferably, the method further includes the step of contacting the bacteria with the compound for which the bacteria have increased susceptibility to. The invention is further relates to the combination of a star shaped peptide polymer and an anti- bacterial compound that restore the sensitivity of antibiotic resistant bacteria to antibiotics that are otherwise ineffective when administered alone.

A new simple and quantitative synthesis of α-aminoacid-N-carboxyanhydrides (oxazolidines-2,5-dione)

Nitrosation of chiral N-carbamoylaminoacids with a mixture of NO and O2 gives, with the same configuration and in quantitative yield the corresponding α-aminoacid-N-carboxyanhydrides (NCA), well known precursors of peptides. The by products of this reaction are N2 and H2O. Copyright (C) 1996 Elsevier Science Ltd.

ENANTIOMERIC QUANTIFICATIONS OF AMINO ACIDS THROUGH THEIR Nα-ACYL AMIDES BY GAS CHROMATOGRAPHY.

Apparent separation of 1.1 or higher on Chiralsil Val III can be obtained for Nα-acyl N-alkyl aminoacid amides allowing the use of short capillary gas chromatographic columns.A clean derivatization protocol without racemization is described, proceding through the NCA derivatives that are prepared from "in situ" silylated amino acids with trimethylsilyl cyanide.