N-Carbobenzoxyalanine 4-nitrophenyl ester

Base Information

• Chemical Name: N-Carbobenzoxyalanine 4-nitrophenyl ester
• CAS No.: 1168-87-2
• Molecular Formula: C17H16 N2 O6
• Molecular Weight: 344.324
• European Community (EC) Number: 214-621-1
• DSSTox Substance ID: DTXSID10922168
• Mol file: 1168-87-2.mol

Synonyms:N-carbobenzoxy-L-alanine 4-nitrophenyl ester;N-carbobenzoxyalanine 4-nitrophenyl ester;N-carbobenzoxyalanine 4-nitrophenyl ester, (D)-isomer;N-CBzAla NPE

Chemical Property of N-Carbobenzoxyalanine 4-nitrophenyl ester

Chemical Property:

• Vapor Pressure: 7.72E-12mmHg at 25°C
• Melting Point: 78-79℃
• Boiling Point: 542.7°C at 760 mmHg
• PKA: 10.66±0.46(Predicted)
• Flash Point: 282°C
• PSA: 110.45000
• Density: 1.315g/cm³
• LogP: 3.72920
• Storage Temp.: -15°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 344.10083623
• Heavy Atom Count: 25
• Complexity: 464

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-L-alanine 4-nitrophenyl ester 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OCC2=CC=CC=C2
• Uses: Z-ALA-ONP is a useful intermediate in the preparation of aza peptides which functions as inhibitors and active site titrants for cysteine proteinases

Technology Process of N-Carbobenzoxyalanine 4-nitrophenyl ester

There total 6 articles about N-Carbobenzoxyalanine 4-nitrophenyl ester 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: 94.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-Cbz-Ala (1142-20-7) → benzyloxycarbonylalanine p-nitrophenyl ester (1168-87-2)

Guidance literature:

With N-ethylmorpholine;; hexamethylphosphorous triamide dichloride; In dichloromethane; 1) 0 deg C, 2 h, 2) overnight, r.t.;

Reference yield:

tris(p-nitrophenyl)-phosphite (23485-35-0) + N-Cbz-Ala (1142-20-7) → benzyloxycarbonylalanine p-nitrophenyl ester (1168-87-2)

Guidance literature:

With pyridine;

DOI:10.1021/ja01524a040

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyloxycarbonylalanine p-nitrophenyl ester (1168-87-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / Et₃N / acetonitrile / 1 h / 5 °C

2: 70 percent / Et₃N / H₂O / 4 h / Ambient temperature; pH=10.0

With triethylamine; In water; acetonitrile;

DOI:10.1246/bcsj.60.2409

upstream raw materials:

tris(p-nitrophenyl)-phosphite

N-Cbz-Ala

4-nitro-phenol

benzyl 4-nitrophenyl carbonate

Downstream raw materials:

benzyloxycarbonyl-L-alanyl-L-alanine

N-(N-carbobenzyloxy-L-alanyl)-L-pyroglutamic acid tert-butyl ester

benzyloxycarbonyl-(S)-alanyl-(S)-histidine methyl ester

Z-Ala-Val-Glu(OBu^t)-Arg-Tyr(Bu^t)-Leu-OH

Refernces

• 1、 -. "COMPOUNDS AND METHODS FOR DELIVERY OF PROSTACYCLIN ANALOGS". Paragraph 0119; 0120. . Retrieved 2015/10/06.
• 2、 Hulsbergen, F. B.,Reedijk, J.. "Coordination compounds of tripeptides and pentapeptides containing L-histidyl residues. Studies towards structural modes for the active site of copper proteins". . p. 278 - 286. Retrieved 2007/10/02.