2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate

Base Information

• Chemical Name: 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate
• CAS No.: 142994-45-4
• Molecular Formula: C₂₃H₂₀N₂O₄
• Molecular Weight: 388.423
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID10931710
• Wikidata: Q72478853
• Mol file: 142994-45-4.mol

Synonyms:DTXSID10931710;2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate

Chemical Property of 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.5E-17mmHg at 25°C
• Melting Point: 166.5 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 645.6 °C at 760 mmHg
• PKA: 3.32±0.10(Predicted)
• Flash Point: 344.3 °C
• PSA: 88.52000
• Density: 1.309 g/cm³
• LogP: 4.00690
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Sparingly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 4.2
• 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-d-3-pyridylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CN=CC=C4)C(=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CN=CC=C4)C(=O)[O-]
• Uses: Fmoc-d-3-pyridylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate

There total 12 articles about 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-(pyridin-3-yl)propanoate 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: 41.0%

N-fluorenylmethyloxycarbonyl-3-pyridylalanine-methyl ester (1397697-66-3) → C24H22N2O4 (1397697-68-5) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid (175453-07-3,142994-45-4)

Guidance literature:

With ammonium hydroxide; α-chymotrypsine; ammonium acetate; In water; N,N-dimethyl-formamide; at 20 ℃; for 2h; pH=6.9; optical yield given as %ee; Enzymatic reaction;

DOI:10.1007/s00726-010-0829-3

Reference yield:

2-amino-3-(pyridin-3-yl)propanoic acid (17470-24-5,28105-69-3,64090-98-8,70702-47-5) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → C23H20N2O4 (746672-88-8,175453-07-3,142994-45-4)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 22h;

DOI:10.1007/s00726-010-0829-3

Reference yield:

2-amino-3-(pyridin-3-yl)propanoic acid (17470-24-5,28105-69-3,64090-98-8,70702-47-5) → C24H22N2O4 (1397697-68-5) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid (175453-07-3,142994-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydrogencarbonate / 1,4-dioxane; water / 22 h / 20 °C

2: chloro-trimethyl-silane / 36 h / 40 °C

3: ammonium hydroxide; α-chymotrypsine; ammonium acetate / water; N,N-dimethyl-formamide / 2 h / 20 °C / pH 6.9 / Enzymatic reaction

With ammonium hydroxide; chloro-trimethyl-silane; α-chymotrypsine; ammonium acetate; sodium hydrogencarbonate; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1007/s00726-010-0829-3

upstream raw materials:

3-pyridinecarboxaldehyde

(4Z)-2-methyl-4((pyridin-3-yl)methylene)oxazol-5(4H)-one

N-acetyl-(β-3-pyridyl)-DL-alanine

N-fluorenylmethyloxycarbonyl-3-pyridylalanine-methyl ester

Downstream raw materials:

HO-Leu-N-Me-Val-D-Leu-D-3-(3-pyridyl)Ala-3,3-diphenyl-D-Ala-NH₂

(S)-2-((S)-2-(3-(3,4-dichlorobenzyl)ureido)-3-(pyridin-3-yl)propanamido)-3-methylbutanoic acid

Refernces