Phenylalanine O-benzyl ester

Base Information

• Chemical Name: Phenylalanine O-benzyl ester
• CAS No.: 58780-66-8
• Molecular Formula: C16H17 N O2 . Cl H
• Molecular Weight: 291.777
• European Community (EC) Number: 219-558-3
• DSSTox Substance ID: DTXSID70275980,DTXSID00914613
• Nikkaji Number: J1.181.300C
• Mol file: 58780-66-8.mol

Synonyms:phenylalanine O-benzyl ester;phenylalanine O-benzyl ester, (DL)-isomer;phenylalanine O-benzyl ester, 4-toulenesulfonate;phenylalanine O-benzyl ester, hydrochloride, (DL)-isomer

Chemical Property of Phenylalanine O-benzyl ester

Chemical Property:

• Boiling Point: 382.8°Cat760mmHg
• Flash Point: 220.3°C
• Density: 1.142g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 255.125928785
• Heavy Atom Count: 19
• Complexity: 268

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)OCC2=CC=CC=C2)N

Technology Process of Phenylalanine O-benzyl ester

There total 7 articles about Phenylalanine O-benzyl 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:

DL-phenylalanine benzyl ester (962-39-0,25282-53-5,47004-38-6) → phenylalanine benzyl ester hydrochloride (58780-66-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; toluene; at 0 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol5028199

Reference yield:

racemic phenylalanine + diethyl ether (60-29-7,927820-24-4) + benzyl chloride (100-44-7) → phenylalanine benzyl ester hydrochloride (58780-66-8)

Guidance literature:

In ethanol; dimethyl sulfoxide;

Reference yield:

benzyl phenyl carbonate (28170-07-2) → phenylalanine benzyl ester hydrochloride (58780-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-diaza-bicyclo[2.2.2]octane / dimethyl sulfoxide / 5 h / 60 °C / Inert atmosphere; Schlenk technique

2: zinc / acetic acid / 16.5 h / 20 °C / Inert atmosphere; Schlenk technique

3: hydrogenchloride / 1,4-dioxane; toluene / 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; zinc; In 1,4-dioxane; acetic acid; dimethyl sulfoxide; toluene;

DOI:10.1021/ol5028199

upstream raw materials:

diethyl ether

benzyl chloride

benzyl phenyl carbonate

2-Phenylnitroethane

Downstream raw materials:

N-phosphono-phenylalanine

L-phenylalanine benzyl ester hydrochloride

(R)-2-amino-3-phenylpropanoic acid benzyl ester hydrochloride

L-phenylalanine

Refernces

• 1、 -. "Esterification process". . . Retrieved 2008/06/13.