CID 6997174

Base Information

• Chemical Name: CID 6997174
• CAS No.: 2188-18-3
• Molecular Formula: C11H21N5O6
• Molecular Weight: 319.318
• Hs Code.: 2925290090
• Mol file: 2188-18-3.mol

Synonyms:

Chemical Property of CID 6997174

Chemical Property:

• Appearance/Colour: white crystal powder
• Melting Point: 257oC
• Refractive Index: 1.564
• PKA: 3.84±0.50(Predicted)
• PSA: 169.36000
• Density: 1.4 g/cm³
• LogP: 1.84580
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Heated)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 319.14918341
• Heavy Atom Count: 22
• Complexity: 434

Purity/Quality:

≥98.0% ^*data from raw suppliers

N-alpha-Boc-N-omega-Nitro-L-arginine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-67-19
• Safety Statements: 26-36-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC[NH+]=C(N)N[N+](=O)[O-])C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC[NH+]=C(N)N[N+](=O)[O-])C(=O)[O-]
• Uses: Boc-L-Nitroarginine, can be used in peptide chemistry. It has been also shown to act as NO synthase inhibitor, and thus used in the study of The effects of methylene blue (MB) for treatment of sepsis induced by bowel perforation.

Technology Process of CID 6997174

There total 12 articles about CID 6997174 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: 95.0%

N-nitro-L-arginine (2149-70-4,13855-78-2,38733-00-5) + di-tert-butyl dicarbonate (24424-99-5) → Boc-Arg(NO2)-OH (2188-18-3)

Guidance literature:

With sodium hydroxide; magnesium oxide; In 1,4-dioxane; water; for 24h; Ambient temperature;

DOI:10.1016/0223-5234(88)90102-X

Reference yield: 85.0%

Nω-nitro-L-arginine (2149-70-4,66036-77-9,137433-32-0) + 1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate (50739-44-1) → N-alpha-t-butoxycarbonyl-Ng-nitroarginine (2188-18-3)

Guidance literature:

With pyridine; sodium hydroxide; In acetone; for 5h; Ambient temperature;

DOI:10.1246/bcsj.56.2974

Reference yield: 82.0%

N-nitro-L-arginine (2149-70-4,13855-78-2,38733-00-5) + tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate (75844-68-7) → Boc-Arg(NO2)-OH (2188-18-3)

Guidance literature:

With dmap; triethylamine; In 1,4-dioxane; water; for 15h; Ambient temperature;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

N-nitro-L-arginine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

t-butylpentachlorophenyl carbonate

Downstream raw materials:

Boc-Arg(NO₂)-Ala-OBzl

C₂₄H₃₈N₆O₇

Refernces

• 1、 Azuse,Tamura,Kinomura,Okai,Kouge,Hamatsu,Koizumi. "Peptide synthesis in aqueous solution. IV. Preparation and properties of [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate and [p-(9-fluorenylmethyl-oxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate as water-soluble N-acylating reagents". . p. 3103 - 3108. Retrieved 2007/10/02.
• 2、 Keller, Oskar,Keller, Walter E.,Van Look, Gert,Wersin, Gernot. "tert-butoxycarbonylation of amino acids and their derivatives: N-tert-butoxycarbonyl-L-phenylalanine". . p. 160 - 160. Retrieved 2017/06/01.