methyl N-acetyltyrosinate

Base Information

• Chemical Name: methyl N-acetyltyrosinate
• CAS No.: 2440-79-1
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20874326
• Nikkaji Number: J1.801.181F
• Mol file: 2440-79-1.mol

Synonyms:methyl N-acetyltyrosinate;23525-90-8;Methyl acetyltyrosinate;methyl 2-acetamido-3-(4-hydroxyphenyl)propanoate;Oprea1_493195;SCHEMBL315117;N-Acetyl-L-Tyrosinemethylester;DTXSID20874326;TYROSINE-N-ACETYL,METHYL ESTER;AKOS003350993;AKOS017258521;N-ACETYL-DL-TYROSINE METHYL ESTER;CS-0361914;FT-0773020;2-(Acetylamino)-3-(4-hydroxyphenyl)propanoic acid methyl ester;2-acetylamino-3-(4-hydroxyphenyl) propionic acid methyl ester

Chemical Property of methyl N-acetyltyrosinate

Chemical Property:

• Vapor Pressure: 5.67E-09mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 457 °C at 760 mmHg
• Flash Point: 230.2 °C
• PSA: 75.63000
• Density: 1.207 g/cm³
• LogP: 1.00330
• Storage Temp.: Store at RT.
• XLogP3: 0.3
• 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:

99% ^*data from raw suppliers

Methyl N-acetyltyrosinate ^*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)O)C(=O)OC
• Uses: Methyl N-Acetyltyrosinate can be used to prepare anti-odor compositions.

Technology Process of methyl N-acetyltyrosinate

There total 30 articles about methyl N-acetyltyrosinate 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: 97.0%

L-Tyr-OMe (1080-06-4) + acetyl chloride (75-36-5) → N-acetyl-L-tyrosine methyl ester (2440-79-1)

Guidance literature:

In tetrahydrofuran; Solvent; Reflux;

Reference yield: 96.0%

N-acetyl-N-methoxyacetamide (128459-09-6) + L-Tyr-OCH3 (1080-06-4) → L-Tyr-OCH3 (2440-79-1,23525-90-8,65160-71-6)

Guidance literature:

In N,N-dimethyl-formamide; for 3.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94382-X

Reference yield: 92.0%

L-Tyr-OMe (1080-06-4) + acetic anhydride (108-24-7) → N-acetyl-L-tyrosine methyl ester (2440-79-1)

Guidance literature:

With acetic acid; at 20 ℃; for 1.08333h; Reflux;

DOI:10.1016/j.tet.2009.05.025

upstream raw materials:

methanol

N-acetyl-L-tyrosine

L-Tyr-OMe

acetic anhydride

Downstream raw materials:

(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphanyloxy)-phenyl]-propionic acid methyl ester

(S)-2-Acetylamino-3-[4-(3-methyl-but-2-enyloxy)-phenyl]-propionic acid methyl ester

N-acetyl-p-(diphenylphosphino)-L-phenylalanine metyl ester

C₁₅H₁₉NO₅

Refernces

• 1、 Goto, Koichi,Yano, Yoshihiro,Okada, Eiji,Liu, Chin-Wen,Yamamoto, Kiyoto,Ueoka, Ryuichi. "Catalytic specificity exhibited by p-sulfonatocalix[n]arenes in the methanolysis of N-acetyl-L-amino acids". . p. 865 - 870. Retrieved 2003.
• 2、 Hernandez, Andres S.,Hodges, John C.. "Solid-Supported tert-Alkoxycarbonylation Reagents for Anchoring of Amines during Solid Phase Organic Synthesis". . p. 3153 - 3157. Retrieved 1997.
• 3、 Kal?ic, Filip,Zgarbová, Michala,Hodek, Jan,Chalupsky, Karel,Dra?ínsky, Martin,Dvo?áková, Alexandra,Strmeň, Timotej,?ebestík, Jaroslav,Baszczyňski, Ond?ej,Weber, Jan,Mertlíková-Kaiserová, Helena,Janeba, Zlatko. "Discovery of Modified Amidate (ProTide) Prodrugs of Tenofovir with Enhanced Antiviral Properties". . p. 16425 - 16449. Retrieved 2021/11/16.
• 4、 Wang, Tao,Hoffmann, Marvin,Dreuw, Andreas,Hasagi?, Edina,Hu, Chao,Stein, Philipp M.,Witzel, Sina,Shi, Hongwei,Yang, Yangyang,Rudolph, Matthias,Stuck, Fabian,Rominger, Frank,Kerscher, Marion,Comba, Peter,Hashmi, A. Stephen K.. "A Metal-Free Direct Arene C?H Amination". supporting information. p. 2783 - 2795. Retrieved 2021/04/05.