N-Carboxylate Melatonin Ethyl Ester

Base Information

• Chemical Name: N-Carboxylate Melatonin Ethyl Ester
• CAS No.: 519186-54-0
• Molecular Formula: C16H20N2O4
• Molecular Weight: 304.341
• DSSTox Substance ID: DTXSID00464880
• Nikkaji Number: J1.864.956J
• Wikidata: Q82290414
• Mol file: 519186-54-0.mol

Synonyms:N-Carboxylate Melatonin Ethyl Ester;519186-54-0;3-[2-(Acetylamino)ethyl]-5-methoxy-1H-indole-1-carboxylic Acid Ethyl Ester;ethyl 3-(2-acetamidoethyl)-5-methoxyindole-1-carboxylate;AGN-PC-008FAG;DTXSID00464880;FT-0664347

Chemical Property of N-Carboxylate Melatonin Ethyl Ester

Chemical Property:

• PSA: 73.05000
• LogP: 3.17340
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 304.14230712
• Heavy Atom Count: 22
• Complexity: 402

Purity/Quality:

98% ^*data from raw suppliers

N-Carboxylate Melatonin Ethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1C=C(C2=C1C=CC(=C2)OC)CCNC(=O)C
• Uses: 3-[2-(AcetylaMino)ethyl]-5-Methoxy-1H-indole-1-carboxylic Acid Ethyl Ester is used in the preparation of 6-hydroxymelatonin (H944625), a human metabolite of melatonin (M215000).

Technology Process of N-Carboxylate Melatonin Ethyl Ester

There total 1 articles about N-Carboxylate Melatonin Ethyl Ester 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: 93.0%

5-methoxy-N-acetyl-tryptamine (73-31-4) + chloroformic acid ethyl ester (541-41-3) → 3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-54-0)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(02)02763-6

Reference yield: 84.0%

acetyl chloride (75-36-5) + 3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-54-0) → N-[2-(6-acetyl-1-carbethoxy-5-methoxyindol-3-yl) ethyl]acetamide (188397-05-9)

Guidance literature:

With aluminium trichloride; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(02)02763-6

Reference yield:

3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-54-0) → 6-hydroxymelatonin (2208-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / aluminum chloride / 1,2-dichloro-ethane / 0.5 h / 20 °C

2: 83 percent / trifluoroacetic acid; m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

3: 65 percent / NaOH / methanol

With sodium hydroxide; aluminium trichloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; 1: Friedel-Crafts acylation / 2: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(02)02763-6

upstream raw materials:

5-methoxy-N-acetyl-tryptamine

chloroformic acid ethyl ester

Downstream raw materials:

N-[2-(6-acetyl-1-carbethoxy-5-methoxyindol-3-yl) ethyl]acetamide

6-hydroxymelatonin

6-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester

Refernces