Methyl N-acetyl-L-tryptophanate

Base Information

• Chemical Name: Methyl N-acetyl-L-tryptophanate
• CAS No.: 2824-57-9
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.293
• UNII: MUP4Y18ZQ5
• DSSTox Substance ID: DTXSID70950962
• Nikkaji Number: J28.028C
• ChEMBL ID: CHEMBL1276128
• Mol file: 2824-57-9.mol

Synonyms:methyl acetyltryptophanate;N-acetyltryptophan methyl ester;N-acetyltryptophan methyl ester, (D)-isomer;N-acetyltryptophan methyl ester, (DL)-isomer

Chemical Property of Methyl N-acetyl-L-tryptophanate

Chemical Property:

• Vapor Pressure: 1.34E-10mmHg at 25°C
• Melting Point: 152.5 °C(Solv: ethyl acetate (141-78-6))
• Refractive Index: 1.599
• Boiling Point: 512.1 °C at 760 mmHg
• PKA: 14.73±0.46(Predicted)
• Flash Point: 263.5 °C
• PSA: 71.19000
• Density: 1.236 g/cm³
• LogP: 1.77900
• Storage Temp.: Store at RT.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 260.11609238
• Heavy Atom Count: 19
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

N-alpha-Acetyl-L-tryptophan methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)OC
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)OC
• Uses: Methyl (2S)-2-aAcetamido-3-(1H-indol-3-yl)propanoate is used in preparation of unsymmetric biaryl sulfides via iron catalyzed regioselective thioarylation of electron-rich arenes with N-(arylthio)succinimides.

Technology Process of Methyl N-acetyl-L-tryptophanate

There total 4 articles about Methyl N-acetyl-L-tryptophanate 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: 99.0%

N-acetyltryptophan methyl ester (2824-57-9,16108-06-8,36060-94-3) → N-AcTrp (1218-34-4) + AcTrpOMe (2824-57-9,16108-06-8,36060-94-3)

Guidance literature:

With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4; In tetrahydrofuran; Ambient temperature;

Reference yield: 92.0%

N-benzoyl-L-tryptophan methyl ester (2717-75-1) → L-tryptophan methyl ester (4299-70-1) + N-acetyl-L-tryptophan methyl ester (2824-57-9,16108-06-8,36060-94-3)

Guidance literature:

With methyl iodide; In methanol; for 24h; Ambient temperature;

DOI:10.1248/cpb.33.3237

Reference yield:

4-nitrophenol acetate (830-03-5) + L-tryptophan methyl ester (4299-70-1) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-acetyl-L-tryptophan methyl ester (2824-57-9,16108-06-8,36060-94-3)

Guidance literature:

β‐cyclodextrin; In water; dimethyl sulfoxide; at 25 ℃; Rate constant; Mechanism; various conditions;

upstream raw materials:

N-benzoyl-L-tryptophan methyl ester

4-nitrophenol acetate

L-tryptophan methyl ester

N-acetyltryptophan methyl ester

Downstream raw materials:

N-acetyl-L-tryptophan methylamide

N^α-acetyl-L-tryptophan-amide

N^α-acetyl-D-tryptophan-methylamide

N-acetyl-D-tryptophan

Refernces

• 1、 Barra, Monica,Rossi, Rita H. de. "Catalysis by β-cyclodextrin in the reaction of p-nitrophenyl acetate with α-amino acids". . p. 1124 - 1130. Retrieved 2007/10/02.