(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

Base Information

Chemical Name:(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate
CAS No.:1380092-30-7
Molecular Formula:C₂₆H₃₃N₃O₇
Molecular Weight:499.564
Hs Code.:

Synonyms:(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

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Chemical Property of (S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

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Technology Process of (S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

There total 5 articles about (S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate 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: 88.0%

: 1380092-15-8
tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate

: 13139-14-5
Boc-Trp-OH

: 1380092-30-7
(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

Guidance literature:: tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h;

Boc-Trp-OH; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.tet.2012.04.024

Reference yield:

: 30225-87-7
2,4,5-trimethoxyphenyl formate

: 1380092-30-7
(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hydroxide / ethanol / 2 h

2.1: trifluoroacetic acid / 20 h / Inert atmosphere; Reflux

2.2: 2 h / Reflux

3.1: tert-butyldimethylsilane; trifluoroacetic acid / acetonitrile / 18 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

4.2: 0 - 20 °C

With tert-butyldimethylsilane; trifluoroacetic acid; potassium hydroxide; In ethanol; dichloromethane; acetonitrile; 2.1: Duff reaction / 2.2: Duff reaction;
DOI:10.1016/j.tet.2012.04.024

Reference yield:

: 4460-86-0,14374-62-0
asaraldehyde

: 1380092-30-7
(S)-tert-butyl 1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C

2.1: potassium hydroxide / ethanol / 2 h

3.1: trifluoroacetic acid / 20 h / Inert atmosphere; Reflux

3.2: 2 h / Reflux

4.1: tert-butyldimethylsilane; trifluoroacetic acid / acetonitrile / 18 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

5.2: 0 - 20 °C

With tert-butyldimethylsilane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; potassium hydroxide; In ethanol; dichloromethane; acetonitrile; 1.1: Baeyer-Villiger oxidation / 3.1: Duff reaction / 3.2: Duff reaction;
DOI:10.1016/j.tet.2012.04.024