Benzyl (S)-[4-[(aminocarbonyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]carbamate

Base Information

• Chemical Name: Benzyl (S)-[4-[(aminocarbonyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]carbamate
• CAS No.: 83575-37-5
• Molecular Formula: C20H23 N5 O6
• Molecular Weight: 429.433
• European Community (EC) Number: 280-492-3
• DSSTox Substance ID: DTXSID801003574
• Wikidata: Q82998168
• Mol file: 83575-37-5.mol

Synonyms:N-benzyloxycarbonyl-L-citrulline para-nitroanilide;N-benzyloxycarbonylcitrulline 4-nitroanilide;Z-Cit 4-NPHA

Chemical Property of Benzyl (S)-[4-[(aminocarbonyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]carbamate

Chemical Property:

• Vapor Pressure: 2.94E-21mmHg at 25°C
• Melting Point: 219 - 220 °C (ethanol)
• Boiling Point: 731.5°C at 760 mmHg
• Flash Point: 396.2°C
• PSA: 168.37000
• Density: 1.357g/cm³
• LogP: 4.35510
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 429.16483347
• Heavy Atom Count: 31
• Complexity: 612

Purity/Quality:

99% ^*data from raw suppliers

Nα-CBZ-L-Citrulline-p-nitroanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCCNC(=O)N)C(=O)NC2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CCCNC(=O)N)C(=O)NC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of Benzyl (S)-[4-[(aminocarbonyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]carbamate

There total 1 articles about Benzyl (S)-[4-[(aminocarbonyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]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: 28.0%

Nα-benzyloxy-carbonyl-L-citrulline (6692-89-3,13594-52-0) + 4-nitro-aniline (100-01-6,104810-17-5) → N1-carbamoyl-3-benzyloxycarbonylamidopiperidin-2-one (83575-38-6) + Nα-benzyloxycarbonyl-L-citrulline p-nitroanilide (83575-37-5)

Guidance literature:

With pyridine; phosphorus trichloride; 1.) -20 deg C, 30 min., 2.) room temp., 30 min., 3.) room temp., 3 days;

DOI:10.1016/0040-4020(82)80232-9

Reference yield:

Nα-benzyloxycarbonyl-L-citrulline p-nitroanilide (83575-37-5) → benzyloxycarbonyl-L-phenylalanyl-L-citrulline p-nitroanilide (83590-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr in HOAc / acetic acid / 1.5 h / Ambient temperature

2: 61 percent / triethylamine / dimethylformamide / 18 h / Ambient temperature

With hydrogen bromide; triethylamine; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(82)80232-9

Reference yield:

Nα-benzyloxycarbonyl-L-citrulline p-nitroanilide (83575-37-5) → L-citrulline p-nitroanilide hydrobromide (83575-39-7)

Guidance literature:

With hydrogen bromide; In acetic acid; for 1.5h; Yield given; Ambient temperature;

DOI:10.1016/0040-4020(82)80232-9

upstream raw materials:

N^α-benzyloxy-carbonyl-L-citrulline

4-nitro-aniline

Downstream raw materials:

L-citrulline p-nitroanilide hydrobromide

Nα-acetyl-L-citrulline p-nitroanilide

Nα-benzoyl-L-citrulline p-nitroanilide

Nα-tosyl-L-citrulline p-nitroanilide