Methyl 2-amino-3-(1H-indol-3-yl)propanoate

Base Information

• Chemical Name: Methyl 2-amino-3-(1H-indol-3-yl)propanoate
• CAS No.: 7303-49-3
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40864547
• Nikkaji Number: J1.485.654D
• ChEMBL ID: CHEMBL5189584
• Mol file: 7303-49-3.mol

Synonyms:1-DL-methyl-tryptophan;methyl tryptophan;methyl tryptophan monohydrochloride, (D-Trp)-isomer;methyl tryptophan monohydrochloride, (DL-Trp)-isomer;methyl tryptophan monohydrochloride, (L-Trp)-isomer;methyl tryptophan, (D-Trp)-isomer;methyl tryptophan, (L-Trp)-isomer;tryptophan methyl ester

Chemical Property of Methyl 2-amino-3-(1H-indol-3-yl)propanoate

Chemical Property:

• Boiling Point: 390.6°Cat760mmHg
• PKA: 17.02±0.30(Predicted)
• Flash Point: 190°C
• PSA: 68.11000
• Density: 1.245g/cm³
• LogP: 1.91100
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

98%min ^*data from raw suppliers

racTryptophanmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CNC2=CC=CC=C21)N

Technology Process of Methyl 2-amino-3-(1H-indol-3-yl)propanoate

There total 38 articles about Methyl 2-amino-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: 100.0%

(R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) → D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2008.05.022

Reference yield: 99.4%

methanol (67-56-1) + D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1)

Guidance literature:

With sulfuric acid; for 2h; Time; Reflux; Large scale;

Reference yield: 94.0%

carbonic acid dimethyl ester (616-38-6) + D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1)

Guidance literature:

With sulfuric acid; at 92 ℃; for 18h;

DOI:10.1039/c3ra45982a

upstream raw materials:

methanol

Trp

methyl tryptophanate hydrochloride

N-(tert-butyloxycarbonyl)-2-(3-indolyl)glycin methyl ester

Downstream raw materials:

(2R)-2-amino-3-(1H-indol-3-yl)propionamide

D-tryptophan

N^α-{4-[bis-(2-chloro-ethyl)-amino]-N-formyl-phenylalanyl}-tryptophan-methyl ester

N^α-trityl-DL-tryptophan-methyl ester

Refernces

• 1、 Lu, Dehua,Qu, Lailiang,Wang, Cheng,Luo, Heng,Li, Shang,Yin, Fucheng,Liu, Xingchen,Chen, Xinye,Luo, Zhongwen,Cui, Ningjie,Peng, Wan,Ji, Limei,Kong, Lingyi,Wang, Xiaobing. "Harmine-based dual inhibitors targeting histone deacetylase (HDAC) and DNA as a promising strategy for cancer therapy". . . Retrieved 2022/01/20.
• 2、 álvarez, Rosana,Alvarez, Susana,Areal, Andrea,De Lera, ángel R.,Domínguez, Marta,Vendrig, Pim. "Total Synthesis of Homo-and Heterodimeric Bispyrrolidinoindoline Dioxopiperazine Natural Products". supporting information. p. 1725 - 1737. Retrieved 2021/06/28.