Fmoc-L-3-(2-pyridyl)-alanine

Base Information

• Chemical Name: Fmoc-L-3-(2-pyridyl)-alanine
• CAS No.: 185379-40-2
• Molecular Formula: C23H20N2O4
• Molecular Weight: 388.423
• Hs Code.: 29223900
• DSSTox Substance ID: DTXSID30426254
• Wikidata: Q72478860
• Mol file: 185379-40-2.mol

Synonyms:Fmoc-L-3-(2-pyridyl)-alanine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-2-ylpropanoate;DTXSID30426254

Chemical Property of Fmoc-L-3-(2-pyridyl)-alanine

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Vapor Pressure: 8.74E-17mmHg at 25°C
• Melting Point: 151 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 630.9 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 335.4 °C
• PSA: 88.52000
• Density: 1.309 g/cm³
• LogP: 4.00690
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Sparingly), Dimethylformamide (Slightly, Sonicated), DMSO (Slig
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 387.13448209
• Heavy Atom Count: 29
• Complexity: 556

Purity/Quality:

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

Fmoc-l-2-pyridylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=CC=N4)C(=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=CC=N4)C(=O)[O-]

Technology Process of Fmoc-L-3-(2-pyridyl)-alanine

There total 6 articles about Fmoc-L-3-(2-pyridyl)-alanine 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: 60.0%

(2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid methyl ester (625096-08-4) → (2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid (185379-40-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b308750f

Reference yield:

2-bromo-pyridine (109-04-6) → (2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid (185379-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Zn; 1,2-dibromoethane; Me₃SiCl / dimethylformamide / 2 h / 35 °C

1.2: 57 percent / Pd(PPh₃)2Cl₂ / dimethylformamide

2.1: 60 percent / aq. LiOH / tetrahydrofuran / 20 °C

With lithium hydroxide; chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b308750f

Reference yield:

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → (2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid (185379-40-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 94 percent / pyridine

2.1: 92 percent / NaI / acetone / 20 °C

3.1: Zn; 1,2-dibromoethane; Me₃SiCl / dimethylformamide / 2 h / 35 °C

3.2: 57 percent / Pd(PPh₃)2Cl₂ / dimethylformamide

4.1: 60 percent / aq. LiOH / tetrahydrofuran / 20 °C

With pyridine; lithium hydroxide; chloro-trimethyl-silane; ethylene dibromide; sodium iodide; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b308750f

upstream raw materials:

(2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid methyl ester

2-bromo-pyridine

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester

Refernces

• 1、 -. "Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same". . . Retrieved 2008/06/13.