N-(3,5-Dinitrobenzoyl)leucine

Base Information

• Chemical Name: N-(3,5-Dinitrobenzoyl)leucine
• CAS No.: 7495-01-4
• Molecular Formula: C13H15 N3 O7
• Molecular Weight: 325.278
• Nikkaji Number: J236.246E
• Mol file: 7495-01-4.mol

Synonyms:DNBL;N-(3,5-dinitrobenzoyl)leucine

Chemical Property of N-(3,5-Dinitrobenzoyl)leucine

Chemical Property:

• Melting Point: 186-188 °C(lit.)
• PSA: 158.04000
• LogP: 3.16940
• Storage Temp.: -20°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 325.09099983
• Heavy Atom Count: 23
• Complexity: 461

Purity/Quality:

99% ^*data from raw suppliers

N-3-5-DINITROBENZOYL-L-LEUCINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
• General Description: N-3-5-DINITROBENZOYL-L-LEUCINE is a chiral compound that serves as a key intermediate in the synthesis of tertiary amine-appended derivatives used as chiral selectors for enantiomer assays. These derivatives, such as (S)-8 and (R)-9, are designed to separate ionization sites from chiral recognition sites, improving enantiomeric discrimination in electrospray ionization mass spectrometry (ESI-MS). N-3-5-DINITROBENZOYL-L-LEUCINE's derivatives enable rapid, concentration-independent, and high-throughput quantitative determination of enantiomeric composition, expanding the range of chiral analytes that can be assayed. This approach complements traditional chiral stationary phase methods and holds potential for discovering new chiral selectors.

Technology Process of N-(3,5-Dinitrobenzoyl)leucine

There total 12 articles about N-(3,5-Dinitrobenzoyl)leucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + 3,5-dinitrobenoyl chloride (99-33-2) → (S)-N-(3,5-dinitrobenzoyl)leucine (7495-01-4)

Guidance literature:

With methyloxirane; In tetrahydrofuran; at 25 ℃; for 0.25h;

DOI:10.1021/jo00191a001

Reference yield: 55.0%

3,5-(NO2)2C6H3CONHCH(CH2CH(CH3)2)COOH (74928-54-4) → (S)-N-(3,5-dinitrobenzoyl)leucine (7495-01-4) + N-(3,5-dinitrobenzoyl)-(R)-leucine (98243-66-4)

Guidance literature:

In 1,1-dichloroethane; water; at 20.84 ℃; for 10h; pH=5.7 - 9; optical yield given as %ee; Resolution of racemate; Centrifugal contactor separators; aq. phosphate buffer;

DOI:10.1021/op900152e

Reference yield:

(R,S)-N-(3,5-dinitrobenzoyl)-leucine methyl ester → (S)-N-(3,5-dinitrobenzoyl)leucine (7495-01-4) + N-(3,5-dinitrobenzoyl)-L-leucine methyl ester (86091-69-2) + N-(3,5-dinitrobenzoyl)-(R)-leucine (98243-66-4) + (R)-2-(3,5-Dinitro-benzoylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:

With sodium hydroxide; N-pivaloyl-(3,5-dimethylphenyl)-L-prolinamide; In hexane; dichloromethane; water; at 0 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol026517s

upstream raw materials:

L-leucine

3,5-dinitrobenoyl chloride

3,5-(NO2)2C6H3CONHCH(CH2CH(CH3)2)COOH

para-bromophenacyl bromide

Downstream raw materials:

N-(3,5-dinitrobenzoyl)-L-leucine methyl ester

2-[(S)-N-(3,5-dinitrobenzoyl)amino-iso-butylacetyl]-2-{[4-allylamino-6-(R)-(1-(1-naphthyl)ethylamino)-1,3,5-triazin-2-yl]oxy}ethylamine

N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide

(S)-(+)-N-(3,5-dinitrobenzoyl)leucine n-propylamide

Refernces

Tertiary amine appended derivatives of N-(3,5-dinitrobenzoyl)leucine as chiral selectors for enantiomer assays by electrospray ionization mass spectrometry

10.1021/ac050438n

The research focuses on the development and application of tertiary amine appended derivatives of N-(3,5-dinitrobenzoyl)leucine as chiral selectors for enantiomer assays using electrospray ionization mass spectrometry (ESI-MS). The purpose of this study was to design chiral selectors that separate the ionization site from the sites required for chiral recognition, thereby enhancing the effectiveness of enantiomeric discrimination. The researchers synthesized chiral selectors (S)-8 and (R)-9 and utilized them in ESI-MS experiments with various chiral analytes. The results demonstrated that the complex intensity fraction in the mass spectra varied linearly with the enantiomeric composition of the analytes, allowing for the quantitative determination of enantiomeric composition. The method proved to be independent of analyte concentration, rapid, and potentially suitable for high-throughput analysis. The chemicals used in this process included the chiral selectors (S)-8 and (R)-9, ammonium chloride as a protonation source, and a range of solvents, primarily methanol and water mixtures, to assess the impact of solvent composition on enantioselectivity. The study concluded that this mass spectrometric method could expand the scope of chiral analytes that can be assayed, complementing the set of analytes that can be enantioresolved on corresponding chiral stationary phases, and could be a valuable tool for discovering new chiral selectors.

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