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%min ^*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-]

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

• 1、 Schuur, Boelo,Hallett, Andrew J.,Winkelman, Jozef G.M.,De Vries, Johannes G.,Heeres, Hero J.. "Scalable enantioseparation of amino acid derivatives using continuous liquid-liquid extraction in a cascade of centrifugal contactor separators". . p. 911 - 914. Retrieved 2009.
• 2、 Susanti,Meinds, Tim G.,Pinxterhuis, Erik B.,Schuur, Boelo,De Vries, Johannes G.,Feringa, Ben L.,Winkelman, Jozef G. M.,Yue, Jun,Heeres, Hero J.. "Proof of concept for continuous enantioselective liquid-liquid extraction in capillary microreactors using 1-octanol as a sustainable solvent". . p. 4334 - 4343. Retrieved 2017.
• 3、 Zhang, Mei,Zi, Min,Wang, Bang-Jin,Yuan, Li-Ming. "Uridine, thymidine and inosine used as chiral stationary phases in HPLC". . p. 2226 - 2228. Retrieved 2014/06/09.