Z-Pro-Phe-OH

Base Information

• Chemical Name: Z-Pro-Phe-OH
• CAS No.: 17350-17-3
• Molecular Formula: C22H24N2O5
• Molecular Weight: 396.443
• European Community (EC) Number: 241-374-7
• Nikkaji Number: J287.016I
• Mol file: 17350-17-3.mol

Synonyms:Z-Pro-Phe-OH;17350-17-3;(S)-2-((S)-1-((Benzyloxy)carbonyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid;(2S)-3-phenyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]propanoic acid;N-benzyloxycarbonyl-L-prolyl-L-phenylalanine;(2S)-3-phenyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidin-2-yl]carbonylamino]propanoic acid;ZP6;Cbz-L-Pro-L-Phe;L-Phenylalanine, N-(1-((phenylmethoxy)carbonyl)-L-prolyl)-;SCHEMBL5710778;BDBM36243;MFCD00037327;N-(N-Benzyloxycarbonyl-L-prolyl)-L-phenylalanine;L-Phenylalanine,1-[(phenylmethoxy)carbonyl]-L-prolyl-;(S)-2-((S)-1-((Benzyloxy)carbonyl)pyrrolidine-2-carboxamido)-3-phenylpropanoicacid;(S)-2-((S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid;(2S)-2-{[(2S)-1-[(BENZYLOXY)CARBONYL]PYRROLIDIN-2-YL]FORMAMIDO}-3-PHENYLPROPANOIC ACID

Chemical Property of Z-Pro-Phe-OH

Chemical Property:

• Vapor Pressure: 5.68E-18mmHg at 25°C
• Refractive Index: 1.603
• Boiling Point: 653.6 °C at 760 mmHg
• Flash Point: 349.1 °C
• PSA: 95.94000
• Density: 1.291 g/cm³
• LogP: 2.92850
• Storage Temp.: -15°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 396.16852187
• Heavy Atom Count: 29
• Complexity: 570

Purity/Quality:

99% ^*data from raw suppliers

Z-Pro-Phe-OH 99+% ^*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)NC(CC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O

Technology Process of Z-Pro-Phe-OH

There total 7 articles about Z-Pro-Phe-OH 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: 98.0%

N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester (23631-72-3) → (S)-2-[(S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido]-3-phenylpropanoic acid (17350-17-3)

Guidance literature:

With sodium hydroxide; In methanol; at 25 ℃;

DOI:10.1021/jm00369a017

Reference yield: 91.0%

benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)tetrahydro-1H-pyrrole-1-carboxylate (886981-23-3) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (S)-2-[(S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido]-3-phenylpropanoic acid (17350-17-3)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo0704255

Reference yield:

N-Benzyloxycarbonyl-L-proline (1148-11-4) → (S)-2-[(S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido]-3-phenylpropanoic acid (17350-17-3)

Guidance literature:

With tetrahydrofuran; chloroformic acid ethyl ester; triethylamine; anschliessend Behandeln mit L-Phenylalanin-methylester in wss. Dioxan und Behandeln des Reaktionsprodukts in Aceton mit wss. NaOH;

DOI:10.1002/hlca.19580410512 DOI:10.1002/hlca.19570400317

upstream raw materials:

N-Benzyloxycarbonyl-L-proline

N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester

benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)tetrahydro-1H-pyrrole-1-carboxylate

L-phenylalanine

Downstream raw materials:

(S)-2-((S)-1-Benzyl-2-isobutoxycarbonyloxy-2-oxo-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

N-L-prolyl-L-phenylalanine

N-(1-benzyloxycarbonyl-L-prolyl)-L-phenylalanine-(4-nitro-benzyl ester)

1,4:3,6-diahydro-5-O-(benzyl)-2-O-(N-carbobenzyloxy-L-proline-L-phenylalanine)-D-mannitol

Refernces

• 1、 Ahmetlli, Ardiol,Spiliopoulou, Nikoleta,Magi-Oikonomopoulou, Angeliki,Gerokonstantis, Dimitrios-Triantaffylos,Moutevelis-Minakakis, Panagiota,Kokotos, Christoforos G.. "Proline dipeptides containing fluorine moieties as oganocatalysts for the asymmetric aldol reaction". . p. 5987 - 5995. Retrieved 2018/09/21.
• 2、 Verardo,Gorassini. "α-N-Protected dipeptide acids: A simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide". . p. 315 - 324. Retrieved 2013/06/05.