methyl L-tryptophanate

Base Information

• Chemical Name: methyl L-tryptophanate
• CAS No.: 4299-70-1
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• European Community (EC) Number: 224-309-7
• DSSTox Substance ID: DTXSID30884057
• Nikkaji Number: J205.692E
• Wikidata: Q27466714
• ChEMBL ID: CHEMBL55830
• Mol file: 4299-70-1.mol

Synonyms:S-Tryptophan methyl ester;Methyl L-tryptophanate;L-Tryptophan, methyl ester (9CI);Tryptophan, methyl ester, L- (7CI,8CI);methyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate;[(1R)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethyl]azanium;L-Tryptophane methyl ester;2-amino-3-(1H-indol-3-yl)propanoic acid methyl ester;Tryptophan methyl ester (6CI);

Chemical Property of methyl L-tryptophanate

Chemical Property:

• Vapor Pressure: 2.62E-06mmHg at 25°C
• Melting Point: 91-92℃
• Boiling Point: 390.6 °C at 760 mmHg
• PKA: 17.02±0.30(Predicted)
• Flash Point: 190 °C
• PSA: 68.11000
• Density: 1.245 g/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:

98.5% ^*data from raw suppliers

L-TryptophanMethylEster ^*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
• Isomeric SMILES: COC(=O)[C@H](CC1=CNC2=CC=CC=C21)N
• Uses: L-Tryptophan Methyl Ester is the acidic-free form of L-Tryptophan Methyl Ester Hydrochloride (T895010), which is an amino acid derivative that may be used to prepare the corresponding amino acid amide L-Trytophanamide Hydrochloride. Also, it is an intermediate used in the synthesis of (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester (B200020), which is a Tadalafil (T004500) derivative and used in the preparation of pyrazinopyridoindole derivatives for their PDE5 inhibitory activity.

Technology Process of methyl L-tryptophanate

There total 58 articles about methyl L-tryptophanate 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%

methanol (67-56-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → L-tryptophan methyl ester (4299-70-1)

Guidance literature:

With thionyl chloride;

DOI:10.3987/com-00-9014

Reference yield: 100.0%

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → L-tryptophan methyl ester (4299-70-1)

Guidance literature:

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

DOI:10.1016/j.bmcl.2008.05.022

Reference yield: 98.0%

methanol (67-56-1) + Boc-Trp-OH (13139-14-5) → L-tryptophan methyl ester (4299-70-1)

Guidance literature:

With sulfuric acid; for 16h; Reflux;

DOI:10.1039/c5ra12063b

upstream raw materials:

methanol

L-Tryptophan

DL-tryptophan methyl ester

N-benzoyl-L-tryptophan methyl ester

Downstream raw materials:

N^α-(N-benzyloxycarbonyl-D-leucyl)-L-tryptophan-methyl ester

L-tryptophanol

L-tryptophanamide

L-Tryptophan

Refernces

• 1、 Liang, Miao-Miao,Ma, Yang-Yang,Zhu, Liang,Jia, Yun-Jing,Zhu, Hua-Jie,Li, Wan,Zhou, Bei-Dou. "Experimental and theoretical investigation of stable diastereomeric conformations of biscarboline amides in solution". . p. 4197 - 4204. Retrieved 2018.
• 2、 Wang, Dan,Neupane, Pratik,Ragnarsson, Lotten,Capon, Robert J.,Lewis, Richard J.. "Synthesis of pseudellone analogs and characterization as novel T-type calcium channel blockers". . . Retrieved 2018.
• 3、 Salehi, Peyman,Babanezhad-Harikandei, Kosar,Bararjanian, Morteza,Al-Harrasi, Ahmed,Esmaeili, Mohammad-Ali,Aliahmadi, Atousa. "Synthesis of novel 1,2,3-triazole tethered 1,3-disubstituted β-carboline derivatives and their cytotoxic and antibacterial activities". . p. 1895 - 1907. Retrieved 2016.
• 4、 Chang, Wei-chen,Sanyal, Dev,Huang, Jhih-Liang,Ittiamornkul, Kuljira,Zhu, Qin,Liu, Xinyu. "In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate". . p. 1208 - 1211. Retrieved 2017.
• 5、 Zheng, Shaojun,Gu, Yongdong,Li, Longbo,Zhu, Rui,Cai, Xingwei,Bai, Hongjin,Zhang, Jiwen. "Synthesis and fungicidal activity of tryptophan analogues–the unexpected calycanthaceous alkaloid derivatives". . p. 1142 - 1149. Retrieved 2017.
• 6、 Zheng, Shaojun,Gu, Yongdong,Zhu, Rui,Li, Longbo,Bai, Hongjin,Zhang, Jiwen. "Synthesis and Antibacterial Activity of Calycanthaceous Alkaloid Derivatives". . p. 127 - 130. Retrieved 2018.
• 7、 Moore, Beth L.,O'Reilly, Rachel K.. "Preparation of chiral amino acid materials and the study of their interactions with 1,1-Bi-2-naphthol". . p. 3567 - 3574. Retrieved 2012.
• 8、 Tokala, Ramya,Mahajan, Surbhi,Kiranmai, Gaddam,Sigalapalli, Dilep Kumar,Sana, Sravani,John, Stephy Elza,Nagesh, Narayana,Shankaraiah, Nagula. "Development of β-carboline-benzothiazole hybrids via carboxamide formation as cytotoxic agents: DNA intercalative topoisomerase IIα inhibition and apoptosis induction". . . Retrieved 2020/12/07.
• 9、 Christmann, Mathias,He, Guoli,List, Benjamin. "Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**". supporting information. p. 13591 - 13596. Retrieved 2021/05/07.