(S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 19647-71-3
• Molecular Formula: C₂₃H₂₁N₃O₅
• Molecular Weight: 419.437
• DSSTox Substance ID: DTXSID80428581
• Wikidata: Q82241406
• Mol file: 19647-71-3.mol

Synonyms:19647-71-3;Z-PHE-PNA;Z-L-Phe-pNA;(S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate;Z-L-Phe p-nitroanilide;benzyl N-[(2S)-1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]carbamate;N-Alpha-Carbobenzoxy-L-phenylalanine-P-nitroanilide;SCHEMBL4011349;DTXSID80428581;JZPHGMKKKDRFSU-NRFANRHFSA-N;MFCD00038114;AKOS024374907;Z-L-PHENYLALANINE p-NITROANILIDE;AS-46852;CS-0333714;F10721;J-012696;L-lysine,compoundwithS-(carboxymethyl)-L-cysteine(1:1);N-alpha-Benzyloxycarbonyl-L-Phenylalanine-p-nitroanilide;Nalpha-[(Benzyloxy)carbonyl]-N-(4-nitrophenyl)-L-phenylalaninamide;(S)-benzyl 1-(4-nitrophenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate;(S)-Benzyl(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate;Benzyl (S)-(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate;Carbamic acid,N-[(1S)-2-[(4-nitrophenyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethylester

Chemical Property of (S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

• Melting Point: 159 °C
• Boiling Point: 696.9±55.0 °C(Predicted)
• PKA: 10.98±0.46(Predicted)
• PSA: 113.25000
• Density: 1.319±0.06 g/cm3(Predicted)
• LogP: 5.05810
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 419.14812078
• Heavy Atom Count: 31
• Complexity: 589

Purity/Quality:

97% ^*data from raw suppliers

Z-L-phenylalanine 4-nitroanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)OCC3=CC=CC=C3
• Uses: Z-L-Phe-pNA is a chromogenic substrate.

Technology Process of (S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

There total 4 articles about (S)-Benzyl (1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 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: 91.0%

N-Cbz-L-Phe (1161-13-3) + 4-nitro-aniline (100-01-6,104810-17-5) → benzyl (S)-(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (14235-15-5,14235-16-6,19647-71-3)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/jo2024703

Reference yield: 91.0%

N-Cbz-L-Phe (1161-13-3) + N,N'-bis(4-nitrophenyl)phospheneimidous amide (134393-23-0) → benzyl (S)-(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (14235-15-5,14235-16-6,19647-71-3)

Guidance literature:

With pyridine; at 40 ℃; for 1.5h;

DOI:10.1246/bcsj.64.1422

Reference yield:

Cbz-D-Phe (2448-45-5) + 4-nitro-aniline (100-01-6,104810-17-5) → benzyl (S)-(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (14235-15-5,14235-16-6,19647-71-3)

Guidance literature:

DOI:10.1248/cpb.33.5301

upstream raw materials:

N-Cbz-L-Phe

N,N'-bis(4-nitrophenyl)phospheneimidous amide

Cbz-D-Phe

4-nitro-aniline

Downstream raw materials:

L-phenylalanine-p-nitroanilide

H-Phe-pNA*HBr

N-Cbz-L-Phe

4-nitro-aniline