Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl ester

Base Information

• Chemical Name: Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl ester
• CAS No.: 5379-97-5
• Molecular Formula: C18H22N2O5
• Molecular Weight: 346.383
• NSC Number: 28328
• DSSTox Substance ID: DTXSID10202073
• Nikkaji Number: J28.026G
• Wikidata: Q83075330
• Mol file: 5379-97-5.mol

Synonyms:BRN 0338581;Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl ester;5379-97-5;Diethyl (acetylamino)(1H-indol-3-ylmethyl)propanedioate;4-22-00-06882 (Beilstein Handbook Reference);C18H22N2O5;NSC28328;SCHEMBL13911074;DTXSID10202073;NSC 28328;NSC-28328;C18-H22-N2-O5;LS-120056;N-acetyl-alpha,alpha-di(ethoxycarbonyl)tryptamine;2-Acetylamino-2-[(1H-indol-3-yl)methyl]malonic acid diethyl ester

Chemical Property of Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl ester

Chemical Property:

• Vapor Pressure: 3.36E-12mmHg at 25°C
• Boiling Point: 551.3°C at 760 mmHg
• Flash Point: 287.2°C
• Density: 1.238g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 346.15287181
• Heavy Atom Count: 25
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CNC2=CC=CC=C21)(C(=O)OCC)NC(=O)C

Technology Process of Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl ester

There total 10 articles about Propanedioic acid, (acetylamino)(1H-indol-3-ylmethyl)-, diethyl 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: 99.5%

3-(Dimethylaminomethyl)indole (87-52-5) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → acetylamino-indol-3-ylmethyl-malonic acid diethyl ester (5379-97-5)

Guidance literature:

With tributylphosphine; In acetonitrile; for 4h; Heating;

Reference yield:

acetylamino-(3-phenylhydrazono-propyl)-malonic acid diethyl ester (6297-96-7) → acetylamino-indol-3-ylmethyl-malonic acid diethyl ester (5379-97-5)

Guidance literature:

With sulfuric acid; chlorobenzene;

Reference yield:

3-(bromomethyl)-1H-indole (50624-64-1) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → acetylamino-indol-3-ylmethyl-malonic acid diethyl ester (5379-97-5)

Guidance literature:

With caesium carbonate; In acetonitrile; at 130 ℃; Microwave irradiation;

DOI:10.1021/acs.orglett.8b02791

upstream raw materials:

3-(Dimethylaminomethyl)indole

2-acetylaminomalonic acid diethyl ester

3-(tert-butyliminomethine)indole

(3-indolylmethyl)trimethylammonium iodide

Downstream raw materials:

N^α-Ethoxycarbonyl-tryptophan

D,L-1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid

Trp

2-amino-3-(1-methyl-1H-indol-3-yl)-propanoic acid

Refernces

• 1、 Howe et al.. "-". . p. 38. Retrieved 1945.
• 2、 Iwao, Masatomo,Motoi, Osamu. "Methodology for the efficient synthesis of 3,4-differentially substituted indoles. Fluoride ion-induced elimination-addition reaction of 1-triisopropylsilylgramine methiodides". . p. 5929 - 5932. Retrieved 2007/10/02.