N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester

Base Information

• Chemical Name: N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester
• CAS No.: 519186-55-1
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.382
• DSSTox Substance ID: DTXSID60458169
• Nikkaji Number: J1.864.957H
• Wikidata: Q82281335
• Mol file: 519186-55-1.mol

Synonyms:519186-55-1;N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester;ethyl 3-(2-acetamidoethyl)-6-acetyloxy-5-methoxyindole-1-carboxylate;3-[2-(Acetylamino)ethyl]-5-methoxy-6-acetyloxy-1H-indole-1-carboxylic Acid Ethyl Ester;AGN-PC-0NHC6D;DTXSID60458169;CAQVWXISGZMXAI-UHFFFAOYSA-N;FT-0664346;3-[2-(Acetylamino)ethyl]-5-methoxy-6-acetoxy-1H-indole-1-carboxylic acid ethyl ester

Chemical Property of N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester

Chemical Property:

• PSA: 99.35000
• LogP: 3.09870
• Solubility.: Methanol
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 362.14778643
• Heavy Atom Count: 26
• Complexity: 526

Purity/Quality:

N-Carboxylate-6-acetyloxy 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=CC(=C(C=C21)OC(=O)C)OC)CCNC(=O)C
• Uses: N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester is used in the preparation of 6-hydroxymelatonin, a human metabolite of Melatonin (M215000).

Technology Process of N-Carboxylate-6-acetyloxy Melatonin Ethyl Ester

There total 3 articles about N-Carboxylate-6-acetyloxy 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: 83.0%

N-[2-(6-acetyl-1-carbethoxy-5-methoxyindol-3-yl) ethyl]acetamide (188397-05-9) → 6-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-55-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

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

Reference yield:

5-methoxy-N-acetyl-tryptamine (73-31-4) → 6-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / sodium hydroxide; tetrabutylammonium hydrogensulfate / CH₂Cl₂ / 1 h / 20 °C

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

3: 83 percent / trifluoroacetic acid; m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; aluminium trichloride; tetra(n-butyl)ammonium hydrogensulfate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane; 2: Friedel-Crafts acylation / 3: Baeyer-Villiger oxidation;

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-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-55-1)

Guidance literature:

Multi-step reaction with 2 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

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

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

upstream raw materials:

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

5-methoxy-N-acetyl-tryptamine

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

Downstream raw materials:

6-hydroxymelatonin

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