(2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid

Base Information

• Chemical Name: (2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid
• CAS No.: 17607-28-2
• Molecular Formula: C11H12FNO3
• Molecular Weight: 225.22
• Hs Code.: 2924299090
• European Community (EC) Number: 241-579-1
• Nikkaji Number: J264.772I
• Mol file: 17607-28-2.mol

Synonyms:DL-Phenylalanine, N-acetyl-3-fluoro-;(2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid;SCHEMBL21037199;69078-51-9;EINECS 241-579-1;AKOS015907793;NSC 270551;N-Acetyl-3-fluoro-3-phenyl-DL-alanine;(S)-2-Acetamido-3-(3-fluorophenyl)propanoic acid;EN300-28274492;A1-52919;330-45-0

Chemical Property of (2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 6.82E-09mmHg at 25°C
• Melting Point: 154-157 °C(lit.)
• Refractive Index: 1.532
• Boiling Point: 450.2 °C at 760 mmHg
• PKA: 3.50±0.10(Predicted)
• Flash Point: 226.1 °C
• PSA: 66.40000
• Density: 1.273 g/cm³
• LogP: 1.34840
• Storage Temp.: Keep Cold
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 225.08012141
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

97% ^*data from raw suppliers

N-Acetyl-3-fluorophenylalanine ^*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: CC(=O)NC(CC1=CC(=CC=C1)F)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC(=CC=C1)F)C(=O)O
• Uses: N-Acetyl-3-fluorophenylalanine is useful in the treatment of cancer as it has neoplasm-inhibiting activity.

Technology Process of (2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid

There total 7 articles about (2S)-2-acetamido-3-(3-fluorophenyl)propanoic acid 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: 99.0%

C11H10FNO3 (599178-62-8) → N-acetyl-3-fluorophenylalanine methyl ester (330-45-0,17607-28-2,69078-51-9)

Guidance literature:

With ((R,R)-1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene)(1,5-cyclooctadiene)rhodium⁽¹⁺⁾hexafluoroantimonate; hydrogen; In methanol; at 20 ℃; for 1h; under 2280.15 Torr;

Reference yield:

(Z)-2-Acetylamino-3-(3-fluoro-phenyl)-acrylic acid → N-acetyl-3-fluorophenylalanine methyl ester (330-45-0,17607-28-2,69078-51-9)

Guidance literature:

With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (S)-O,O'-(1,1'-dinaph-2,2'diyl)-N-Me₂P-amidite; In dichloromethane; at 20 ℃; for 2h; under 7500.75 Torr;

DOI:10.1002/adsc.200390026

Reference yield:

diethyl α-acetamido, α-(3-fluorobenzyl)malonate (380-70-1) → N-acetyl-3-fluorophenylalanine methyl ester (330-45-0,17607-28-2,69078-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous NaOH / anschliessend Erhitzen mit wss. HCl

2: papain

With sodium hydroxide; papain;

DOI:10.1021/ja01160a113

upstream raw materials:

phenylhydrazine

diethyl α-acetamido, α-(3-fluorobenzyl)malonate

C₁₁H₁₀FNO₃

Downstream raw materials:

3-fluorophenylalanine

N-acetyl-3-fluorophenylalanine methyl ester

N-acetyl-3-fluoro-L-phenylalanine-(N'-phenyl-hydrazide)

L-4-fluorophenylalanine