N-Acetyl-O-methyl-L-tyrosine

Base Information

• Chemical Name: N-Acetyl-O-methyl-L-tyrosine
• CAS No.: 28047-05-4
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40450146
• Nikkaji Number: J1.164.287J
• Wikidata: Q82269734
• Mol file: 28047-05-4.mol

Synonyms:28047-05-4;AC-TYR(ME)-OH;N-Acetyl-O-methyl-L-tyrosine;(2S)-2-ACETAMIDO-3-(4-METHOXYPHENYL)PROPANOIC ACID;N-acetyl-O-methyltyrosine;(S)-2-Acetamido-3-(4-methoxyphenyl)propanoic acid;Acetyl-O-methyl-L-tyrosine;Ac-L-Tyr(Me)-OH;O-Methyl-N-acetyl-tyrosin;SCHEMBL4361126;DTXSID40450146;N-Acetyl-4-methoxy-L-phenylalanine;MFCD00026170;AKOS024324462;EN300-7391838

Chemical Property of N-Acetyl-O-methyl-L-tyrosine

Chemical Property:

• Melting Point: 150-151 °C
• Boiling Point: 487.5±40.0 °C(Predicted)
• PKA: 3.17±0.10(Predicted)
• PSA: 75.63000
• Density: 1.206±0.06 g/cm3(Predicted)
• LogP: 1.21790
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 272

Purity/Quality:

98%min ^*data from raw suppliers

Acetyl-O-methyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=C(C=C1)OC)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC=C(C=C1)OC)C(=O)O

Technology Process of N-Acetyl-O-methyl-L-tyrosine

There total 13 articles about N-Acetyl-O-methyl-L-tyrosine 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%

(Z)-2-acetamido-3-(4-methoxyphenyl)-2-propenoic acid (73549-09-4) → (S)-N-acetyl-p-methoxyphenylalanine (28047-05-4)

Guidance literature:

With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane; In tetrahydrofuran; at 20 ℃; for 24h; under 750.075 Torr;

Reference yield: 69.0%

O-Methyltyrosine (6230-11-1) + acetic anhydride (108-24-7) → (S)-N-acetyl-p-methoxyphenylalanine (28047-05-4)

Guidance literature:

With sodium carbonate; sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 2h;

DOI:10.1039/c3cc49580a

Reference yield:

(Z)-2-acetamido-3-(4-methoxyphenyl)-2-propenoic acid (73549-09-4) → (S)-N-acetyl-p-methoxyphenylalanine (28047-05-4) + (D)-N-acetyl-4-methoxy-phenylalanine (70601-62-6)

Guidance literature:

With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (3R,4R)-(+)-3,4-Bis(diphenylphosphino)tetrahydrofuran; In methanol; toluene; for 40h; under 3750.3 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1055/s-1992-26275

upstream raw materials:

(S)-N-acetyl-3-(4-methoxyphenyl)alanine methyl ester

acetic anhydride

L-tyrosine

(Z)-2-acetamido-3-(4-methoxyphenyl)-2-propenoic acid

Downstream raw materials:

Ac-L-Tyr(Me)-L-Ala-NH₂

Ac-L-Tyr(Me)-D-Ala-NH₂

Ac-L-Tyr(Me)-L-Ala-OH

Ac-L-Tyr(Me)-D-Ala-OH

Refernces

• 1、 Guzow, Katarzyna,Ganzynkowicz, Robert,Rzeska, Alicja,Mrozek, Justyna,Szabelski, Mariusz,Karolczak, Jerzy,Liwo, Adam,Wiczk, Wies?aw. "Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations". . p. 3879 - 3889. Retrieved 2004.
• 2、 Arava, Veera Reddy,Amasa, Srinivasulu Reddy,Goud Bhatthula, Bharat Kumar,Kompella, Laxmi Srinivas,Matta, Venkata Prasad,Subha. "Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate". . p. 2892 - 2897. Retrieved 2013/09/02.