2-Acetamido-3-(4-phenylmethoxyphenyl)propanoic acid

Base Information

• Chemical Name: 2-Acetamido-3-(4-phenylmethoxyphenyl)propanoic acid
• CAS No.: 73535-46-3
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• European Community (EC) Number: 667-927-6
• Mol file: 73535-46-3.mol

Synonyms:N-Acetyl-O-benzyl-L-tyrosine;Oprea1_651923;Oprea1_868138;AKOS005349980

Chemical Property of 2-Acetamido-3-(4-phenylmethoxyphenyl)propanoic acid

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 385

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-ACETYL-O-BENZYL-L-TYROSINE AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=C(C=C1)OCC2=CC=CC=C2)C(=O)O

Technology Process of 2-Acetamido-3-(4-phenylmethoxyphenyl)propanoic acid

There total 10 articles about 2-Acetamido-3-(4-phenylmethoxyphenyl)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: 81.2%

N-acetyl-O-benzyl-L-tyrosine methyl ester (39613-68-8) → N-ac-(O-benzyl)tyrosine (73535-46-3)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2012.08.014

Reference yield: 78.0%

N-acetyl-L-tyrosine (537-55-3) + benzyl chloride (100-44-7) → N-ac-(O-benzyl)tyrosine (73535-46-3)

Guidance literature:

N-acetyl-L-tyrosine; benzyl chloride; With sodium methylate; tetra-(n-butyl)ammonium iodide; In methanol; at 40 ℃; for 24h;

With hydrogenchloride; In methanol; water;

Reference yield:

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) → N-ac-(O-benzyl)tyrosine (73535-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / diethyl ether

2: Et₃N / dioxane

With hydrogenchloride; triethylamine; In 1,4-dioxane; diethyl ether; 1: Hydrolysis / 2: Acetylation;

DOI:10.1002/(SICI)1520-6017(200001)89:1<108::AID-JPS11>3.0.CO;2-A

upstream raw materials:

acetic anhydride

Fmoc-Tyr(tBu)-OH

benzyl alcohol

O-benzyl-S-tyrosine

Downstream raw materials:

C₁₈H₂₀N₂O₄

[1S-[1R*[R*(R*)]]]-2-[2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-N-(1-dihexylcarbamoyl-ethyl)-3-methyl-butyramide