(S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester
• CAS No.: 274677-49-5
• Molecular Formula: C₂₁H₂₂N₂O₅
• Molecular Weight: 382.416

Synonyms:(S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

Chemical Property of (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

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Technology Process of (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

There total 1 articles about (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl 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:

syringic aldehyde (134-96-3) + L-tryptophan methyl ester (4299-70-1) → (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester (274677-49-5)

Guidance literature:

With trimethyl orthoformate; In dichloromethane; for 18.5h;

DOI:10.1021/jm9905662

Reference yield: 95.0%

(S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester (274677-49-5) → 2-(4-hydroxy-3,5-dimethoxy-benzylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; at 20 ℃; for 44h;

DOI:10.1021/jm9905662

Reference yield:

(S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester (274677-49-5) → (1R,3S)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (274677-69-9) + (1S,3S)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (274677-68-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jm9905662

upstream raw materials:

syringic aldehyde

L-tryptophan methyl ester

Downstream raw materials:

(1R,3S)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

(1S,3S)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

2-[(9H-fluoren-9-ylmethoxycarbonylamino)-acetyl]-1-(4-hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

2-[(9H-fluoren-9-ylmethoxycarbonylamino)-acetyl]-1-(4-hydroxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

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