4-Amino-L-phenyl-N-phthalylalanine ethyl ester

Base Information

• Chemical Name: 4-Amino-L-phenyl-N-phthalylalanine ethyl ester
• CAS No.: 74743-23-0
• Molecular Formula: C19H18N2O4
• Molecular Weight: 338.363
• Hs Code.: 2925190090
• European Community (EC) Number: 277-979-8
• DSSTox Substance ID: DTXSID901132895
• Nikkaji Number: J349.455A
• Mol file: 74743-23-0.mol

Synonyms:NSC313359;ethyl (2S)-3-(4-aminophenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate;3-(4-aminophenyl)-2-(1,3-diketoisoindolin-2-yl)propionic acid ethyl ester;(S)-α-[(4-Aminophenyl)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid ethyl ester;

Chemical Property of 4-Amino-L-phenyl-N-phthalylalanine ethyl ester

Chemical Property:

• Vapor Pressure: 1.64E-11mmHg at 25°C
• Melting Point: 102-103 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Refractive Index: 1.637
• Boiling Point: 534.8 °C at 760 mmHg
• PKA: 4.42±0.10(Predicted)
• Flash Point: 277.2 °C
• PSA: 89.70000
• Density: 1.331 g/cm³
• LogP: 2.55830
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 338.12665706
• Heavy Atom Count: 25
• Complexity: 504

Purity/Quality:

99% ^*data from raw suppliers

(S)-Ethyl3-(4-Aminophenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CC=C(C=C1)N)N2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: CCOC(=O)[C@H](CC1=CC=C(C=C1)N)N2C(=O)C3=CC=CC=C3C2=O

Technology Process of 4-Amino-L-phenyl-N-phthalylalanine ethyl ester

There total 10 articles about 4-Amino-L-phenyl-N-phthalylalanine ethyl ester 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: 100.0%

N-phthalimido-4-nitro-L-phenylalanine ethyl ester (17451-67-1) → N-phthalimido-4-amino-L-phenylalanine ethyl ester (74743-23-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 30 ℃; for 0.16h; under 15001.5 Torr; Autoclave;

Reference yield:

p-nitro-L-phenylalanine hydrate (207569-25-3,444777-67-7,207591-86-4) → N-phthalimido-4-amino-L-phenylalanine ethyl ester (74743-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / toluene / 3 h / Reflux

2: thionyl chloride / 3 h / Reflux

3: palladium on activated charcoal; hydrogen / ethanol; water

With thionyl chloride; palladium on activated charcoal; hydrogen; triethylamine; In ethanol; water; toluene;

Reference yield:

phthalic anhydride (85-44-9) → N-phthalimido-4-amino-L-phenylalanine ethyl ester (74743-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / toluene / 3 h / Reflux

2: thionyl chloride / 3 h / Reflux

3: palladium on activated charcoal; hydrogen / ethanol; water

With thionyl chloride; palladium on activated charcoal; hydrogen; triethylamine; In ethanol; water; toluene;

upstream raw materials:

N-phthalimido-4-nitro-L-phenylalanine ethyl ester

N-(2-carboxy-benzoyl)-4-nitro-L-phenylalanine ethyl ester

p-nitro-L-phenylalanine hydrate

phthalic anhydride

Downstream raw materials:

4-(2-chloro-ethylamino)-L-phenylalanine ethyl ester

4-benzylamino-L-phenylalanine

4-[benzyl-(2-chloro-ethyl)-amino]-L-phenylalanine

4-(2-hydroxy-ethylamino)-N,N-phthaloyl-L-phenylalanin-ethyl ester

Refernces

• 1、 -. "Melphalan intermediate and preparation method thereof". Paragraph 0043; 0079-0083; 0107; 0143-0147; 0171; 0207-0211. . Retrieved 2019/08/02.
• 2、 -. "Synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester". Paragraph 0032; 0033; 0047-0048; 0060-0061; 0076-0077. . Retrieved 2017/10/28.