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

Base Information

• Chemical Name: 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid
• CAS No.: 1137-00-4
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.216
• Hs Code.: 2933990090
• European Community (EC) Number: 672-717-2
• NSC Number: 19495
• UNII: 26NJJ3M0J5
• DSSTox Substance ID: DTXSID101229652
• Nikkaji Number: J207.917H
• Mol file: 1137-00-4.mol

Synonyms:7-azatryptophan;7-azatryptophan, (+-)-isomer;7-azatryptophan, (S)-isomer

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

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 1.73E-09mmHg at 25°C
• Melting Point: 259 °C
• Refractive Index: 1.709
• Boiling Point: 466.1 °C at 760 mmHg
• Flash Point: 235.7 °C
• PSA: 92.00000
• Density: 1.434 g/cm³
• LogP: 1.21760
• Storage Temp.: −20°C
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 205.085126602
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%,99%, ^*data from raw suppliers

D,L-7-Aza-3-indolylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2CC(C(=O)O)N)N=C1

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

There total 32 articles about 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid 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: 75.0%

ethyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate → 7-azatryptophan (7303-50-6,1137-00-4)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1074/jbc.M116.741561

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: 70.0%

C19H21N3O2 → (-)-(R)-7-azatryptophan (134235-82-8,1137-00-4) + (S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (49758-35-2,1137-00-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 8h; under 3040.2 Torr;

DOI:10.1002/bkcs.10287

upstream raw materials:

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate

7-azagramine

7-Azaindole

N,N,N-trimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanaminium iodide

Downstream raw materials:

2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethylamine

C₂₂H₂₁N₅O₂

C₂₂H₂₂N₆O

3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

Refernces

• 1、 Gee, Moon Bae,Kim, Tae Seung,Yum, Eul Kgun. "Palladium-catalyzed heteroannulation approach to 7-azatryptophan with a Sch?llkopf chiral auxiliary". . p. 1546 - 1549. Retrieved 2015.
• 2、 Nakano, Shogo,Minamino, Yuki,Hasebe, Fumihito,Ito, Sohei. "Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase". . p. 10152 - 10158. Retrieved 2019/10/19.