2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic Acid

Base Information

• Chemical Name: 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic Acid
• CAS No.: 71953-90-7
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.293
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50391379
• Mol file: 71953-90-7.mol

Synonyms:71953-90-7;N-ACETYL-5-METHYL-DL-TRYPTOPHAN;Ac-5-Me-DL-Trp-OH;2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic Acid;Tryptophan,N-acetyl-5-methyl-;NALPHA-ACETYL-5-METHYL-DL-TRYPTOPHAN;(R)-2-Acetamido-3-(5-methyl-1H-indol-3-yl)propanoic acid;SCHEMBL5717906;N-Acetyl-5-methyl-L-tryptophan;DTXSID50391379;GTCLKZDZUKYDDV-UHFFFAOYSA-N;150357-14-5;MFCD00055984;MFCD31692926;AKOS024324499;AG-G-82682;AS-48757;SY301170;FT-0629802;A-1500;F53230;114872-77-4

Chemical Property of 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic Acid

Chemical Property:

• Vapor Pressure: 1.2E-14mmHg at 25°C
• Refractive Index: 1.633
• Boiling Point: 587.5 °C at 760 mmHg
• Flash Point: 309.1 °C
• PSA: 82.19000
• Density: 1.292 g/cm³
• LogP: 1.99900
• Storage Temp.: Store at 0°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 260.11609238
• Heavy Atom Count: 19
• Complexity: 359

Purity/Quality:

98%Min ^*data from raw suppliers

N-alpha-Acetyl-5-methyl-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC=C2CC(C(=O)O)NC(=O)C
• Uses: N-Acetyl-5-methyl-dl-tryptophan is a useful reagent for the preparation of lactone ketolide macrolide erythromycin antibiotics.

Technology Process of 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic Acid

There total 4 articles about 2-acetamido-3-(5-methyl-1H-indol-3-yl)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: 29.0%

5-methyl-DL-tryptophan (951-55-3) + acetic anhydride (108-24-7) → 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic acid (71953-90-7)

Guidance literature:

In methanol; at 40 ℃; for 16h;

DOI:10.1016/j.bmcl.2021.128085

Reference yield:

acetylamino-(5-methyl-indol-3-ylmethyl)-malonic acid diethyl ester (114872-67-2) → 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic acid (71953-90-7)

Guidance literature:

With sodium hydroxide; Erwaermen des Reaktionsprodukts mit H₂O;

DOI:10.1021/ja01104a028

Reference yield:

L-serin (56-45-1,83245-15-2) + 5-methyl-1H-indole (614-96-0) + acetic anhydride (108-24-7) → 2-acetamido-3-(5-methyl-1H-indol-3-yl)propanoic acid (71953-90-7)

Guidance literature:

With acetic acid; at 80 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/jm5002925

upstream raw materials:

acetylamino-(5-methyl-indol-3-ylmethyl)-malonic acid diethyl ester

L-serin

5-methyl-1H-indole

acetic anhydride

Downstream raw materials:

D,L-5-methyltryptophan