methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]propanoate

Base Information

• Chemical Name: methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]propanoate
• CAS No.: 19779-75-0
• Molecular Formula: C19H18N2O2
• Molecular Weight: 306.364
• DSSTox Substance ID: DTXSID50369492
• Nikkaji Number: J284.895C
• Mol file: 19779-75-0.mol

Synonyms:19779-75-0;methyl 2-(benzylideneamino)-3-(1H-indol-3-yl)propanoate;methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]propanoate;D,L-Tryptophan Methyl Ester Benzaldimine;Maybridge1_006745;Oprea1_560544;SCHEMBL7530573;HMS560K13;DTXSID50369492;LFMPJRXYSNSSJV-UHFFFAOYSA-N;CCG-52021;FT-0675707;D,L-TRYPTOPHAN METHYL ESTER, BENZALDIMINE;SR-01000641279-1;2-Benzylideneamino-3-(1H-indol-3-yl)propionic acid methyl ester

Chemical Property of methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]propanoate

Chemical Property:

• Melting Point: 125-126°C
• PSA: 54.45000
• LogP: 3.37110
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 306.136827821
• Heavy Atom Count: 23
• Complexity: 418

Purity/Quality:

95% ^*data from raw suppliers

D,L-Tryptophan methyl ester, benzaldimine ^*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=CC3=CC=CC=C3
• Uses: Optically active α-amino acid derivative.

Technology Process of methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]propanoate

There total 10 articles about methyl 3-(1H-indol-3-yl)-2-[(phenylmethylene)amino]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: 95.7%

benzaldehyde (100-52-7) + DL-tryptophan methyl ester (7303-49-3) → Nb-Benzylidenetryptophan methyl ester (19779-75-0)

Guidance literature:

In benzene; for 1h; Heating;

DOI:10.1021/jo00189a008

Reference yield: 95.0%

methyl tryptophanate hydrochloride (5619-09-0,7524-52-9,14907-27-8,26988-71-6,41222-70-2,67557-19-1,109492-62-8) + benzaldehyde (100-52-7) → (E)-2-(benzylidene-amino)-3-(1H-indol-3-yl)-propionic acid methyl ester (19779-75-0,67628-15-3)

Guidance literature:

methyl tryptophanate hydrochloride; With magnesium sulfate; triethylamine; In dichloromethane; at 20 ℃; for 1h;

benzaldehyde; In dichloromethane; at 20 ℃;

DOI:10.1021/ja807669q

Reference yield: 91.0%

(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) + benzaldehyde (100-52-7) → Nb-benzylidene-L-tryptophan methyl ester (19779-75-0,67628-15-3)

Guidance literature:

(S)-tryptophan methyl ester hydrochloride; With magnesium sulfate; triethylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

benzaldehyde; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.7b04690

upstream raw materials:

benzaldehyde

DL-tryptophan methyl ester

methyl tryptophanate hydrochloride

(S)-tryptophan methyl ester hydrochloride

Downstream raw materials:

4-indol-3-ylmethyl-1,3-dioxo-6ξ-phenyl-(3ar,6ac)-hexahydro-furo[3,4-c]pyrrole-4ξ-carboxylic acid methyl ester

trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene

cis-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene

(1R,3S,3aR,6aS)-methyl 1-((1H-indol-3-yl)methyl)-octahydro-5-methyl-4,6-dioxo-3-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate