ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate

Base Information

• Chemical Name: ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate
• CAS No.: 42717-06-6
• Molecular Formula: C15H18N2O3
• Molecular Weight: 274.32
• NSC Number: 201443
• DSSTox Substance ID: DTXSID00308018
• Nikkaji Number: J2.605.984D
• Mol file: 42717-06-6.mol

Synonyms:42717-06-6;Acetyl-L-tryptophan ethyl ester;ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate;NSC201443;Ethyl 2-(acetylamino)-3-(1H-indol-3-yl)propanoate #;Ethyl acetyl-DL-tryptophanate;SCHEMBL850315;DTXSID00308018;KQGQONPKSKUHHT-UHFFFAOYSA-N;Tryptophan, N-acetyl, ethyl ester;AKOS015963035;Ethyl N(alpha)-acetyl-dl-tryptophanate;NSC-201443;AC-19243;FT-0634237

Chemical Property of ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate

Chemical Property:

• Boiling Point: 517.6°Cat760mmHg
• Flash Point: 266.8°C
• Density: 1.208g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 274.13174244
• Heavy Atom Count: 20
• Complexity: 359

Purity/Quality:

99%min ^*data from raw suppliers

ethyl2-acetamido-3-(1H-indol-3-yl)propanoate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate

There total 13 articles about ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate 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: 55.0%

N-Acetyl-2,3-dihydro-Trp-OEt (68262-53-3) → acetyltryptophan ethylester (42717-06-6)

Guidance literature:

With oxygen; salcomine; In methanol; at 25 ℃; for 24h;

DOI:10.1246/cl.1980.1287

Reference yield: 45.0%

ethyl 2-acetamido-4-(2-aminophenyl)pent-4-enoate → acetyltryptophan ethylester (42717-06-6)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; trifluoroacetic acid; In methanol; at 60 ℃; for 44h; Electrolysis; Glovebox; Sealed tube;

DOI:10.1039/d1cc05882g

Reference yield: 30.0%

2-Acetylamino-3-[2-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionic acid ethyl ester (154048-79-0) → acetyltryptophan ethylester (42717-06-6)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/0040-4039(93)85073-6

upstream raw materials:

ethyl 2-((1H-indol-3-yl)methyl)-3-oxobutanoate

acetylamino-indol-3-ylmethyl-malonic acid diethyl ester

ethanol

N-acetyl-DL-tryptophan

Downstream raw materials:

N-acetyl-L-tryptophane ethyl ester

N-acetyl-D-tryptophan ethyl ester

N-AcTrp

N-acetyl-D-tryptophan

Refernces

• 1、 Chang, Sukbok,Kim, Dongwook,Kim, Youyoung. "Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles". supporting information. p. 12309 - 12312. Retrieved 2021/12/07.
• 2、 Stella, Selvaraj,Chadha, Anju. "Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330". experimental part. p. 457 - 460. Retrieved 2010/06/21.