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

Base Information

• Chemical Name: 3-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-phenylpropanoate
• CAS No.: 209252-15-3
• Molecular Formula: C24H21NO4
• Molecular Weight: 387.43
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID80943188
• Wikidata: Q72477952
• Mol file: 209252-15-3.mol

Synonyms:DTXSID80943188;3-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-phenylpropanoate

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

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Vapor Pressure: 4.43E-16mmHg at 25°C
• Melting Point: 187.3 °C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 617 °C at 760 mmHg
• PKA: 4.27±0.10(Predicted)
• Flash Point: 326.9 °C
• PSA: 75.63000
• Density: 1.275 g/cm³
• LogP: 5.13200
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 386.13923312
• Heavy Atom Count: 29
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-D-beta-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)[O-])NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CC(=O)[O-])NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

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

There total 5 articles about 3-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-phenylpropanoate 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: 84.0%

Nα-Fmoc-D-phenylglycinyldiazomethane → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropionic acid (209252-15-3)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; at 70 ℃; for 6h;

DOI:10.1081/SCC-120002414

Reference yield:

(S)-3-amino-3-phenylpropanoic acid (614-19-7,3646-50-2,13921-90-9,40856-44-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropionic acid (209252-15-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1002/poc.1328

Reference yield:

N-Fmoc-D-phenylglycine (111524-95-9,163883-97-4) → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropionic acid (209252-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TsCl; Py / tetrahydrofuran / 0.25 h / 0 °C

1.2: 92 percent / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

2.1: 84 percent / C₆H₅CO₂Ag / dioxane; H₂O / 6 h / 70 °C

With pyridine; silver benzoate; p-toluenesulfonyl chloride; In tetrahydrofuran; 1,4-dioxane; water; 2.1: Wolff rearrangement;

DOI:10.1081/SCC-120002414

upstream raw materials:

N-Fmoc-D-phenylglycine

(S)-3-amino-3-phenylpropanoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

N-Fmoc-β-Phe-Ac₆c-Asn-(O^tBu)

C₂₇H₃₆N₄O₅

C₂₇H₃₆N₄O₅

C₂₇H₃₆N₄O₅