7-Methoxy-1-methyl-D-tryptophan ethyl ester

Base Information

• Chemical Name: 7-Methoxy-1-methyl-D-tryptophan ethyl ester
• CAS No.: 655239-35-3
• Molecular Formula: C15H20N2O3
• Molecular Weight: 276.335
• DSSTox Substance ID: DTXSID70471460
• Nikkaji Number: J1.999.276D
• Wikidata: Q82299972
• Mol file: 655239-35-3.mol

Synonyms:655239-35-3;7-METHOXY-1-METHYL-D-TRYPTOPHAN ETHYL ESTER;DTXSID70471460;Ethyl 7-methoxy-1-methyl-D-tryptophanate

Chemical Property of 7-Methoxy-1-methyl-D-tryptophan ethyl ester

Chemical Property:

• PSA: 66.48000
• LogP: 2.32010
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 276.14739250
• Heavy Atom Count: 20
• Complexity: 337

Purity/Quality:

97% ^*data from raw suppliers

7-METHOXY-1-METHYL-D-TRYPTOPHAN ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CN(C2=C1C=CC=C2OC)C)N
• Isomeric SMILES: CCOC(=O)[C@@H](CC1=CN(C2=C1C=CC=C2OC)C)N

Technology Process of 7-Methoxy-1-methyl-D-tryptophan ethyl ester

There total 5 articles about 7-Methoxy-1-methyl-D-tryptophan ethyl ester 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: 90.0%

methyl iodide (74-88-4) + (5R,2S)-3,6-diethoxy-2-isopropyl-5-[7-methoxy-2-(triethylsilyl)-3-indolyl]methyl-2,5-dihydropyrazine (655240-14-5) → Na-methyl-7-methoxy-D-tryptophan ethyl ester (655239-35-3)

Guidance literature:

methyl iodide; (5R,2S)-3,6-diethoxy-2-isopropyl-5-[7-methoxy-2-(triethylsilyl)-3-indolyl]methyl-2,5-dihydropyrazine; In N,N-dimethyl-formamide;

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/ol0362212

Reference yield:

(2S,5R)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine (355839-49-5) → Na-methyl-7-methoxy-D-tryptophan ethyl ester (655239-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Pd(OAc)2; LiCl; K₂CO₃ / dimethylformamide / 36 h / 100 °C

2: NaH / dimethylformamide / 1.5 h / 0 °C

3: 1.69 g / aq. HCl / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; palladium diacetate; sodium hydride; potassium carbonate; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo052081t

Reference yield:

2-iodo-6-methoxybenzenamine (354574-31-5) → Na-methyl-7-methoxy-D-tryptophan ethyl ester (655239-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Pd(OAc)2; LiCl; K₂CO₃ / dimethylformamide / 36 h / 100 °C

2: NaH / dimethylformamide / 1.5 h / 0 °C

3: 1.69 g / aq. HCl / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; palladium diacetate; sodium hydride; potassium carbonate; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo052081t

upstream raw materials:

methyl iodide

(5R,2S)-3,6-diethoxy-2-isopropyl-5-[7-methoxy-2-(triethylsilyl)-3-indolyl]methyl-2,5-dihydropyrazine

(2S,5R)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine

2-iodo-6-methoxybenzenamine

Downstream raw materials:

2-benzylamino-3-(7-methoxy-1-methyl-1H-indol-3-yl)-propionic acid ethyl ester

C₂₃H₂₄N₂O₂

(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

Refernces

• 1、 Zhou, Hao,Liao, Xuebin,Cook, James M.. "Regiospecific, Enantiospecific Total Synthesis of the 12-Alkoxy- Substituted Indole Alkaloids, (+)-12-Methoxy-Na-methylvellosimine, (+)-12-Methoxyaffinisine, and (-)-Fuchsiaefoline". . p. 249 - 252. Retrieved 2007/10/03.