BOC-L-4-Nitrophe

Base Information

• Chemical Name: BOC-L-4-Nitrophe
• CAS No.: 33305-77-0
• Molecular Formula: C14H18N2O6
• Molecular Weight: 310.307
• Hs Code.: 29242990
• European Community (EC) Number: 251-450-1
• DSSTox Substance ID: DTXSID30908424
• Nikkaji Number: J319.522H
• Wikidata: Q82877832
• Mol file: 33305-77-0.mol

Synonyms:Alanine,N-carboxy-3-(p-nitrophenyl)-, N-tert-butyl ester, L- (8CI);(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-nitrophenyl)propanoic acid;(S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-nitrophenyl)propionic acid;2-(S)-[(tert-Butoxycarbonyl)amino]-3-(4-nitrophenyl)propionic acid;N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine;N-(tert-Butyloxycarbonyl)-p-nitro-L-phenylalanine;N-Boc-p-nitro-L-phenylalanine;N-tert-Butoxycarbonyl-p-nitro-L-phenylalanine;Boc-4-Nitro-Phe-OH;Boc-Phe(4-NO2)-OH;Boc-Phe(4-NO2);

Chemical Property of BOC-L-4-Nitrophe

Chemical Property:

• Appearance/Colour: Faintly yellow powder
• Vapor Pressure: 3.4E-11mmHg at 25°C
• Melting Point: 107 °C
• Refractive Index: 1.553
• Boiling Point: 509.3oC at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 261.8oC
• PSA: 121.45000
• Density: 1.29 g/cm3
• LogP: 3.02930
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 310.11648630
• Heavy Atom Count: 22
• Complexity: 418

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-p-nitro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O
• Uses: N-Boc-p-nitro-L-phenylalanine is the N-Boc protected form of p-Nitro-L-phenylalanine (N502725, Hydrate) and is a useful synthetic intermediate in the synthesis of Hydroxymelphalan (H939850); an analog of Melphalan (M216900) which is an antineoplastic.

Technology Process of BOC-L-4-Nitrophe

There total 14 articles about BOC-L-4-Nitrophe 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-nitro-3-phenyl-L-alanine (949-99-5) → Boc-Phe(p-NO2)-OH (33305-77-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 3h; Ambient temperature;

DOI:10.1021/jo951855a

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-4-nitro-phenylalanine (56613-61-7) → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2006.03.021

Reference yield: 86.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (R)-4-nitro-phenylalanine (56613-61-7) → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 18h;

DOI:10.1016/S0968-0896(97)00130-2

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

4-nitro-3-phenyl-L-alanine

di-tert-butyl dicarbonate

{[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile

Downstream raw materials:

N-(tert-butyloxycarbonyl)-4-nitro-L-phenylalanine ethyl ester

Boc-dmaPhe-OH

(S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester

(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester