Benzoyl-L-citrulline methyl ester

Base Information

• Chemical Name: Benzoyl-L-citrulline methyl ester
• CAS No.: 14325-36-1
• Molecular Formula: C14H19 N3 O4
• Molecular Weight: 293.323
• Hs Code.: 2924299090
• European Community (EC) Number: 238-273-5
• DSSTox Substance ID: DTXSID30931792
• Nikkaji Number: J216.963K
• Wikidata: Q82907372
• Mol file: 14325-36-1.mol

Synonyms:14325-36-1;Benzoyl-L-citrulline methyl ester;Bz-Cit-OMe;(S)-Methyl 2-benzamido-5-ureidopentanoate;methyl (2S)-2-benzamido-5-(carbamoylamino)pentanoate;EINECS 238-273-5;Methyl N5-(aminocarbonyl)-N2-benzoyl-L-ornithine;METHYL (2S)-5-(CARBAMOYLAMINO)-2-(PHENYLFORMAMIDO)PENTANOATE;DTXSID30931792;MFCD00038142;AKOS027340154;Methyl (S)-2-benzamido-5-ureidopentanoate;CS-0337264;(S)-2-Bz-amino-5-ureidopentanoic acid methyl ester;J-007782;L-Ornithine,n5-(aminocarbonyl)-n2-benzoyl-,methyl ester;N-(5-{[Hydroxy(imino)methyl]amino}-1-methoxy-1-oxopentan-2-yl)benzenecarboximidic acid

Chemical Property of Benzoyl-L-citrulline methyl ester

Chemical Property:

• Vapor Pressure: 1.94E-11mmHg at 25°C
• Boiling Point: 533°Cat760mmHg
• Flash Point: 276.1°C
• PSA: 110.52000
• Density: 1.21g/cm³
• LogP: 1.88860
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 293.13755610
• Heavy Atom Count: 21
• Complexity: 367

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Methyl2-benzamido-5-ureidopentanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCCNC(=O)N)NC(=O)C1=CC=CC=C1
• Isomeric SMILES: COC(=O)[C@H](CCCNC(=O)N)NC(=O)C1=CC=CC=C1

Technology Process of Benzoyl-L-citrulline methyl ester

There total 5 articles about Benzoyl-L-citrulline methyl ester 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: 84.0%

methanol (67-56-1) + Nα-benzoyl-L-citrulline (10334-68-6) → Nα-benzoyl-L-citrulline methyl ester (14325-36-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00295a022

Reference yield: 29.0%

Nα-benzoyl-Nδ-cyanoornithine methyl ester (125735-07-1) + DL-aspartic acid dimethyl ester hydrochloride (32213-95-9) → Nα-benzoyl-L-citrulline methyl ester (14325-36-1) + (Nα-benzoylarginino)succinic acid trimethyl ester (125735-08-2) + Nα-benzoylarginine methyl ester hydrochloride (96955-27-0)

Guidance literature:

In water; acetonitrile; for 40h; Heating; pH 2.5, other ester;

DOI:10.1021/jo00295a022

Reference yield: 16.0%

Nα-benzoyl-Nδ-cyanoornithine methyl ester (125735-07-1) + DL-aspartic acid dimethyl ester hydrochloride (32213-95-9) → Nα-benzoyl-L-citrulline methyl ester (14325-36-1) + (Nα-benzoylarginino)succinic acid trimethyl ester (125735-08-2)

Guidance literature:

In water; acetonitrile; for 10h; Heating; pH 3.7;

DOI:10.1021/jo00295a022

upstream raw materials:

N^α-benzoyl-L-ornithine

urethane

methanol

N^α-benzoyl-L-citrulline

Downstream raw materials:

N^α-benzoyl-N^δ-cyanoornithine methyl ester

N^α-benzoylarginine methyl ester hydrochloride

(N^α-benzoylarginino)succinic acid trimethyl ester

Bz-Cit-NH2

Refernces

• 1、 Ranganathan,Rathi. "Urea cycle: Chemical simulation of arginine biosynthesis". . p. 2351 - 2354. Retrieved 2007/10/02.