L-Ornithine, N2-methyl-

Base Information

• Chemical Name: L-Ornithine, N2-methyl-
• CAS No.: 16748-29-1
• Molecular Formula: C₆H₁₄N₂O₂
• Molecular Weight: 146.189
• UNII: 95YQ110TMJ
• DSSTox Substance ID: DTXSID50426397
• Nikkaji Number: J2.015.661I
• Wikidata: Q72493953
• Mol file: 16748-29-1.mol

Synonyms:L-Ornithine, N2-methyl-;16748-29-1;N2-Methyl-L-ornithine;(2S)-5-amino-2-(methylamino)pentanoic acid;N-Me-Orn-OH;95YQ110TMJ;methylornithine;UNII-95YQ110TMJ;SCHEMBL161214;DTXSID50426397;AKOS006349683;(2S)-2-(Methylamino)-5-aminopentanoic acid

Chemical Property of L-Ornithine, N2-methyl-

Chemical Property:

• PSA: 75.35000
• LogP: 1.29110
• Storage Temp.: Store at RT.
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 146.105527694
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

98%Min ^*data from raw suppliers

N-Me-Orn-OH 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(CCCN)C(=O)O
• Isomeric SMILES: CN[C@@H](CCCN)C(=O)O

Technology Process of L-Ornithine, N2-methyl-

There total 13 articles about L-Ornithine, N2-methyl- 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:

(S)-2-Benzylamino-5-(toluene-4-sulfonylamino)-pentanoic acid → Nα-Methyl-L-ornithin (16748-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCO₂H

2: H₂, aq. HCl / Pd-C / acetic acid

3: aq. HBr / Heating

With hydrogenchloride; formic acid; hydrogen bromide; hydrogen; palladium on activated charcoal; In acetic acid;

DOI:10.1021/jm00274a030

Reference yield:

Nα-Benzyl-Nα-methyl-Nε-tosyl-l-ornithin (37149-04-5) → Nα-Methyl-L-ornithin (16748-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, aq. HCl / Pd-C / acetic acid

2: aq. HBr / Heating

With hydrogenchloride; hydrogen bromide; hydrogen; palladium on activated charcoal; In acetic acid;

DOI:10.1021/jm00274a030

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-cyanobutyric acid (161561-59-7) → Nα-Methyl-L-ornithin (16748-29-1)

Guidance literature:

(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-cyanobutyric acid; With platinum(IV) oxide; hydrogen; In methanol; under 1551.49 Torr;

With hydrogenchloride; for 4h; Further stages.;

DOI:10.1016/j.tetlet.2004.01.047

upstream raw materials:

N⁵-benzoyl-N²-methyl-N²-(toluene-4-sulfonyl)-L-ornithine

N^α-Methyl-N^ε-p-toluensulfonyl-l-ornithin

(S)-5-Acetylamino-2-[methyl-(toluene-4-sulfonyl)-amino]-pentanoic acid isopropyl ester

(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-cyanobutyric acid

Refernces

• 1、 Hlavacek, Jan,Fric, Ivo,Budesinsky, Milos,Blaha, Karel. "AN ALTERNATIVE ROUTE TO Nα-METHYLAMINO ACID DERIVATIVES: SYNTHESIS AND CONFORMATION OF SOME Nα-acetyl-Nα-METHYLAMINO ACID METHYLAMIDES". . p. 2473 - 2494. Retrieved 2007/10/02.
• 2、 Skinner,Johansson. "Ornithine analogs as potential ornithine decarboxylase inhibitors 1. N-Substituted ornithine derivatives.". . p. 427 - 428. Retrieved 2007/10/05.