BOC-ALA-ONP

Base Information

• Chemical Name: BOC-ALA-ONP
• CAS No.: 2483-49-0
• Molecular Formula: C14H18N2O6
• Molecular Weight: 310.307
• European Community (EC) Number: 219-621-5
• DSSTox Substance ID: DTXSID30947737
• Mol file: 2483-49-0.mol

Synonyms:Alanine,N-carboxy-, N-tert-butyl p-nitrophenyl ester (7CI);Alanine, N-carboxy-,N-tert-butyl p-nitrophenyl ester, L- (8CI);BOC-L-Alanine p-nitrophenyl ester;N-(tert-Butyloxycarbonyl)-L-alanine p-nitrophenyl ester;N-tert-Butoxycarbonyl-L-alanine p-nitrophenyl ester;p-NitrophenylN-tert-butoxycarbonyl-L-alaninate;p-Nitrophenyl N-tert-butyloxycarbonyl-L-alaninate;p-Nitrophenyl tert-butoxycarbonyl-L-alaninate;tert-Butyloxycarbonyl-L-alaninep-nitrophenyl ester;Boc-Ala-ONP;

Chemical Property of BOC-ALA-ONP

Chemical Property:

• Vapor Pressure: 1.12E-08mmHg at 25°C
• Melting Point: 78 °C(Solv: methanol (67-56-1))
• Refractive Index: 1.528
• Boiling Point: 460.9 °C at 760 mmHg
• PKA: 10.87±0.46(Predicted)
• Flash Point: 232.6 °C
• PSA: 110.45000
• Density: 1.237 g/cm³
• LogP: 3.32750
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 310.11648630
• Heavy Atom Count: 22
• Complexity: 418

Purity/Quality:

98% ^*data from raw suppliers

Boc-L-alanine-4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C

Technology Process of BOC-ALA-ONP

There total 5 articles about BOC-ALA-ONP 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: 85.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + L-N-Boc-Ala (15761-38-3) → tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester (2483-49-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.tet.2009.07.048

Reference yield:

L-N-Boc-Ala (15761-38-3) + 1-nitro-4-trifluoroacetoxy-benzene (658-78-6) → tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester (2483-49-0)

Guidance literature:

With pyridine;

DOI:10.1246/bcsj.38.1979

Reference yield:

tert-Butyl 4-nitrophenyl carbonate (13303-10-1) + sodium L-alaninate (16480-55-0,18463-04-2,23338-69-4,32342-58-8) → tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester (2483-49-0)

Guidance literature:

Multistep reaction; (i), (ii) DCC;

DOI:10.1039/j39670000689

upstream raw materials:

4-nitro-phenol

L-N-Boc-Ala

[(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

1-nitro-4-trifluoroacetoxy-benzene

Downstream raw materials:

4-nitro-phenol

N-(tert-butyloxycarbonyl)-(S)-alanylglycine

Boc-Ala-Lys(Z)-OH

Boc-L-Ala-L-Ser(Bzl)-OH

Refernces

• 1、 Ke, Damei,Zhan, Chuanlang,Li, Xiao,Li, Alexander D. Q.,Yao, Jiannian. "A simple synthesis of imide-dipeptides". experimental part. p. 1506 - 1510. Retrieved 2009/12/24.
• 2、 Goodnow Jr.,Konno,Niwa,Kallimopoulos,Bukownik,Lenares,Nakanishi. "Synthesis of glutamate receptor antagonist philanthotoxin-433 (PhTX-433) and its analogs". . p. 3267 - 3286. Retrieved 2007/10/02.