(S)-2-Acetamido-3-(4-acetoxyphenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-Acetamido-3-(4-acetoxyphenyl)propanoic acid
• CAS No.: 17355-23-6
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Hs Code.: 2924299090
• European Community (EC) Number: 241-383-6
• UNII: 2YW8SXH2W8
• DSSTox Substance ID: DTXSID90938404
• Nikkaji Number: J287.020G
• Wikidata: Q82914715
• Mol file: 17355-23-6.mol

Synonyms:N,O-diacetyltyrosine

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

Chemical Property:

• Vapor Pressure: 1.72E-11mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 512.6 °C at 760 mmHg
• Flash Point: 263.8 °C
• PSA: 92.70000
• Density: 1.261g/cm³
• LogP: 1.13460
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 265.09502258
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

N,O-Bis-acetyl-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(=O)C)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC=C(C=C1)OC(=O)C)C(=O)O
• Uses: N,O-Diacetyl-L-tyrosine is used in biological studies asa model for acyltyrosine residue in creatine kinase modified by nucleotide imidazolides.

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

There total 4 articles about (S)-2-Acetamido-3-(4-acetoxyphenyl)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: 48.0%

acetic anhydride (108-24-7) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → N-acetyl-O-acetyl-L-tyrosine (17355-23-6)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 0.75h; pH=6 - 8;

DOI:10.1002/anie.201509863

Reference yield:

(Z)-α-Acetamido-p-acetyloxycinnamic Acid (64896-34-0) → N-acetyl-O-acetyl-L-tyrosine (17355-23-6) + O,N-diacetyltyrosine (61478-30-6)

Guidance literature:

With hydrogen; triethylamine; Rh(I)-phosphine 22; In ethanol; at 20 ℃; under 41371.8 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00327a023

Reference yield:

4-acetoxy-α-acetylamino-cinnamic acid (52507-18-3) → N-acetyl-O-acetyl-L-tyrosine (17355-23-6) + O,N-diacetyltyrosine (61478-30-6)

Guidance literature:

With hydrogen; ClO4; (2R,3S)-1,2-bis(diphenylphosphino)-3-tBoc-aminobutane; In ethanol; for 22h; Yield given; Ambient temperature;

upstream raw materials:

acetic anhydride

L-tyrosine

Ketene

4-acetoxy-α-acetylamino-cinnamic acid

Downstream raw materials:

L-tyrosine

4-(2-acetamido-3-oxobutyl)phenyl acetate

(S)-2-({1-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-cyclopentanecarbonyl}-amino)-3-hydroxy-propionic acid methyl ester

1-{(S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-cyclopentanecarboxylic acid ethyl ester

Refernces

• 1、 Terfort. "Synthesis and application of (3R,4R)-3,4-bis(diphenylphosphino)tetrahydrofuran as ligand for asymmetric hydrogenation of acrylic acids". . p. 951 - 953. Retrieved 2007/10/02.
• 2、 Saito, Kunio,Saijo, Shigeyoshi,Kotera, Keishi,Date, Tadamasa. "Asymmetric Hydrogenation Catalyzed by Rhodium Complex with a New Chiral Bisphosphine Derived from L-Threonine". . p. 1342 - 1350. Retrieved 2007/10/02.