(2S)-2-azaniumyl-3-(1-methylindol-3-yl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(1-methylindol-3-yl)propanoate
• CAS No.: 21339-55-9
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• Pharos Ligand ID: Y9W9AZWCNZ6S
• Mol file: 21339-55-9.mol

Synonyms:

Chemical Property of (2S)-2-azaniumyl-3-(1-methylindol-3-yl)propanoate

Chemical Property:

• Vapor Pressure: 3.92E-08mmHg at 25°C
• Melting Point: >300 °C (dec.)(lit.)
• Refractive Index: 1.625
• Boiling Point: 429.3 °C at 760 mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 213.4 °C
• PSA: 68.25000
• Density: 1.284 g/cm³
• LogP: 1.83300
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly, Sonicated), DMSO (Sl
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

(S)-2-Amino-3-(1-methyl-1h-indol-3-yl)propanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: CN1C=C(C2=CC=CC=C21)C[C@@H](C(=O)[O-])[NH3+]
• Uses: 1-Methyl-L-tryptophan can be used:In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N2-arylation of 1,2,3-triazoles.As a key starting material for the total synthesis of (?)-ardeemin.In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.

Technology Process of (2S)-2-azaniumyl-3-(1-methylindol-3-yl)propanoate

There total 7 articles about (2S)-2-azaniumyl-3-(1-methylindol-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: 92.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + methyl iodide (74-88-4) → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

L-Tryptophan; With iron(III) nitrate monohydrate; ammonia; sodium; at -60 ℃;

methyl iodide; In diethyl ether;

DOI:10.1021/jo802216z

Reference yield: 85.0%

N-tert-butyloxycarbonyl-L-1-methyltryptophan methyl ester → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 5h;

Reference yield:

2-dibenzylamino-3-(1-methyl-1H-indol-3-yl)-propionic acid benzyl ester → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

With palladium on activated charcoal; ammonium formate; In tetrahydrofuran; methanol; water; for 12h; Heating;

DOI:10.1016/S0960-894X(02)00345-1

upstream raw materials:

L-Tryptophan

methyl iodide

1-methylindole

L-serin

Downstream raw materials:

(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1-methyl-1H-indol-3-yl)propanoic acid

Nα-[2-cyano-3-(2-fluorophenyl)acryloyl]-1-methyl-L-tryptophan

Nα-[3-(2-cyanophenyl)acryloyl]-1-methyl-L-tryptophan

N-in-methyl-L-tryptophan n-heptyl ester tosylate

Refernces

• 1、 -. "Method for synthesizing 1 - methyl - L L-tryptophan (by machine translation)". Paragraph 0008; 0009. . Retrieved 2020/08/02.
• 2、 Katayev, Dmitry,Larionov, Evgeny,Nakanishi, Masafumi,Besnard, Cline,Kündig, E. Peter. "Palladium-N-heterocyclic carbene (NHC)-catalyzed asymmetric synthesis of indolines through regiodivergent C(sp3)-H activation: Scope and DFT study". supporting information. p. 15021 - 15030. Retrieved 2015/02/19.