diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate

Base Information

• Chemical Name: diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate
• CAS No.: 211179-97-4
• Molecular Formula: C17H20N3O5
• Molecular Weight: 347.371
• DSSTox Substance ID: DTXSID80421254
• Nikkaji Number: J962.031A
• Mol file: 211179-97-4.mol

Synonyms:211179-97-4;Diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate;diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate;Ethyl alpha-Acetamido-alpha-carbethoxy-beta-(7-aza-3-indolyl)propionate;ETHYL A-ACETAMIDO-A-CARBETHOXY-B-(7-AZA-3-INDOLYL)PROPIONATE;Ethyl |A-Acetamido-|A-carbethoxy-|A-(7-aza-3-indolyl)propionate;SCHEMBL17596482;DTXSID80421254;CWXWWNREJHXTSJ-UHFFFAOYSA-N;MFCD03425557;STK929914;AKOS005660058;BS-47974;CS-0151550;FT-0668129;D81306;A934769;Ethyl ?-Acetamido-?-carbethoxy-?-(7-aza-3-indolyl)propionate;diethyl (acetylamino)(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate;(Acetylamino)[(1H-pyrrolo[2,3-b]pyridine-3-yl)methyl]malonic acid diethyl ester;Ethyl alpha -Acetamido- alpha -carbethoxy- beta -(7-aza-3-indolyl)propionate

Chemical Property of diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate

Chemical Property:

• Melting Point: 95-130°C
• PSA: 113.87000
• LogP: 1.94680
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Dichloromethane, Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 347.14812078
• Heavy Atom Count: 25
• Complexity: 493

Purity/Quality:

97% ^*data from raw suppliers

Ethylα-Acetamido-α-carbethoxy-β-(7-aza-3-indolyl)propionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CNC2=C1C=CC=N2)(C(=O)OCC)NC(=O)C
• Uses: An unusual alpha-amino acid with a very potent fluorescent activity. Its used as a vehicle for probing the structure and dynamics of protein and peptides. Ethyl α-Acetamido-α-carbethoxy-β-(7-aza-3-indolyl)propionate is an unusual alpha-amino acid with a very potent fluorescent activity. It is used as a vehicle for probing the structure and dynamics of protein and peptides.

Technology Process of diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate

There total 1 articles about diethyl 2-acetamido-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)propanedioate 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: 50.4%

7-azagramine (5654-92-2) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate (211179-97-4)

Guidance literature:

With sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 15h; Reflux; Inert atmosphere;

Reference yield: 72.5%

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate (211179-97-4) → 7-azatryptophan (7303-50-6,1137-00-4)

Guidance literature:

With hydrogenchloride; In water; for 15h; Reflux;

Reference yield:

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate (211179-97-4) → Nα-Acetyl-DL-7-azatryptophan (63024-18-0)

Guidance literature:

With hydrogenchloride; sodium hydroxide; Yield given. Multistep reaction; 1.) dioxane, 40 deg C, 1 day, 2.) dioxane, reflux, 15 h;

DOI:10.1016/S0957-4166(98)00130-X

upstream raw materials:

7-azagramine

2-acetylaminomalonic acid diethyl ester

Downstream raw materials:

7-azatryptophan

N^α-Acetyl-DL-7-azatryptophan

(-)-(R)-7-azatryptophan

(S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

Refernces