N-Cbz-DL-Leucine p-nitrophenyl ester

Base Information

• Chemical Name: N-Cbz-DL-Leucine p-nitrophenyl ester
• CAS No.: 1738-87-0
• Molecular Formula: C20H22N2O6
• Molecular Weight: 386.404
• Hs Code.: 2924299090
• NSC Number: 139977
• Mol file: 1738-87-0.mol

Synonyms:N-Cbz-DL-Leucine p-nitrophenyl ester;Z-L-Leu-ONp;Carbobenzoxy-L-leucine p-nitrophenyl ester;4108-19-4;L-Leucine, 4-nitrophenyl ester;SCHEMBL10366989;(4-nitrophenyl) 4-methyl-2-(phenylmethoxycarbonylamino)pentanoate;NSC139977;NSC-139977;Leucine, N-benzyl p-nitrophenyl ester, L-;FT-0633811;N-Carbobenzoxy-L-leucine p-nitrophenyl ester;Benzyloxycarbonyl-L-leucine p-nitrophenyl ester;N-(Benzyloxycarbonyl)leucine p-nitrophenyl ester;N-(Benzyloxycarbonyl)-L-leucine p-nitrophenyl ester;4-nitrophenyl 2-(benzyloxycarbonylamino)-4-methylpentanoate

Chemical Property of N-Cbz-DL-Leucine p-nitrophenyl ester

Chemical Property:

• Appearance/Colour: Off white to yellowish powder
• Vapor Pressure: 1.26E-12mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 561.3 °C at 760 mmHg
• PKA: 10.66±0.46(Predicted)
• Flash Point: 293.2 °C
• PSA: 110.45000
• Density: 1.239 g/cm³
• LogP: 4.75540
• Storage Temp.: 2-8°C
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 386.14778643
• Heavy Atom Count: 28
• Complexity: 519

Purity/Quality:

99% ^*data from raw suppliers

Z-L-leucine 4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OCC2=CC=CC=C2

Technology Process of N-Cbz-DL-Leucine p-nitrophenyl ester

There total 5 articles about N-Cbz-DL-Leucine p-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: 85.0%

Z-Leu-OH (2018-66-8) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Z-Leu-ONp (1738-87-0)

Guidance literature:

With dmap; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1039/c39850000473

Reference yield:

Z-Leu-OH (2018-66-8) + 4-Nitrophenyl chloroformate (7693-46-1) → Z-Leu-ONp (1738-87-0)

Guidance literature:

With dmap; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) 0 deg C, 30 min;

DOI:10.1021/jo00205a004

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Z-Leu-ONp (1738-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride; diethyl ether; pyridine

2: pyridine

With pyridine; thionyl chloride; diethyl ether;

DOI:10.1002/hlca.19570400216

upstream raw materials:

Z-Leu-OH

4-nitro-phenol

bis(p-nitrophenyl)sulfite

4-Nitrophenyl chloroformate

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-leucyl)-D-phenylalanine ethyl ester

Benzyloxycarbonylleucyl-glycine ethyl ester

L-Leu-ONp

Z-Leu-Val-OMe

Refernces

• 1、 Kim, Sunggak,Ko, Young Kwan. "A New Method for the Preparation of Active Esters Using Di-2-pyridyl Carbonate". . p. 473. Retrieved 2007/10/02.
• 2、 Pozdnev, V. F.,Chernaya, M. Yu.. "ACTIVATION OF A CARBOXY GROUP BY DIALKYL PYROCARBONATES. SYNTHESIS OF SYMMETRICAL ANHYDRIDES AND ARYL ESTERS OF N-PROTECTED AMINO ACIDS USING DI-tert-BUTYL PYROCARBONATE AS CONDENSING REAGENT". . p. 333 - 337. Retrieved 2007/10/02.