Carbobenzyloxy-L-proline p-nitrophenyl ester

Base Information

• Chemical Name: Carbobenzyloxy-L-proline p-nitrophenyl ester
• CAS No.: 3304-59-4
• Molecular Formula: C19H18 N2 O6
• Molecular Weight: 370.362
• NSC Number: 88179
• DSSTox Substance ID: DTXSID50954660
• Mol file: 3304-59-4.mol

Synonyms:Carbobenzyloxy-L-proline p-nitrophenyl ester;EINECS 221-981-3;BRN 0056776;L-Proline, carbobenzyloxy-, p-nitrophenyl ester;1-Benzyl p-nitrophenyl L-1,2-pyrrolidinedicarboxylate;SCHEMBL11599392;DTXSID50954660;GXUFIJVKXYWCAO-UHFFFAOYSA-N;NSC88179;1,2-Pyrrolidinedicarboxylic acid, 1-benzyl p-nitrophenyl ester, L-;NSC-88179;FT-0634770;N-carbobenzoxy-DL-proline p-nitrophenyl ester;4-22-00-00037 (Beilstein Handbook Reference);A821583;1-benzyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate;pyrrolidine-1,2-dicarboxylic acid O2-(4-nitrophenyl) ester O1-(phenylmethyl) ester

Chemical Property of Carbobenzyloxy-L-proline p-nitrophenyl ester

Chemical Property:

• Appearance/Colour: White to slightly yellow crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 541.7 °C at 760 mmHg
• Flash Point: 281.4 °C
• PSA: 101.66000
• Density: 1.356 g/cm³
• LogP: 3.76250
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 370.11648630
• Heavy Atom Count: 27
• Complexity: 535

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)OC3=CC=C(C=C3)[N+](=O)[O-]

Technology Process of Carbobenzyloxy-L-proline p-nitrophenyl ester

There total 8 articles about Carbobenzyloxy-L-proline 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: 88.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N-benzyloxycarbonyl-L-proline p-nitrophenyl ester (3304-59-4)

Guidance literature:

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

Reference yield:

ethyl 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetate (41844-58-0) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N-benzyloxycarbonyl-L-proline p-nitrophenyl ester (3304-59-4)

Guidance literature:

With triethylamine; In ethyl acetate;

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-benzyloxycarbonyl-L-proline p-nitrophenyl ester (3304-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH

2: dicyclohexylcarbodiimide

With sodium hydroxide; dicyclohexyl-carbodiimide;

DOI:10.1021/ja981775z

upstream raw materials:

4-nitro-phenol

N-Benzyloxycarbonyl-L-proline

tris(p-nitrophenyl)-phosphite

4-Nitrophenyl chloroformate

Downstream raw materials:

L-proline p-nitrophenyl ester hydrogen bromide

(S)-benzyl 2-((S)-2-(methoxycarbonyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

(S)-2-Cyclohexylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

N-carbobenzyloxy-L-prolyl-L-proline p-nitrophenyl ester

Refernces

• 1、 Diakos, Connie I.,Zhang, Mei,Beale, Philip J.,Fenton, Ronald R.,Hambley, Trevor W.. "Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)". experimental part. p. 2807 - 2814. Retrieved 2009/10/10.
• 2、 Arena, Giuseppe,Impellizzeri, Giuseppe,Maccarrone, Giuseppe,Pappalardo, Giuseppe,Sciotto, Domenico,Rizzarelli, Enrico. "Thermodynamic and (1)H NMR Study of Proton Complex Formation of Histidine-containing Cyclodipeptides in Aqueous Solution". . p. 371 - 376. Retrieved 2007/10/02.