1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

Base Information

Chemical Name:1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
CAS No.:294862-42-3
Molecular Formula:C₃₂H₄₃N₅O₄Si
Molecular Weight:589.81
Hs Code.:

Synonyms:1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

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Chemical Property of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

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Technology Process of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

There total 7 articles about 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide 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: 92.5%

: 1929-29-9
3-(4-methoxyphenyl)propanoic acid

: 294862-31-0
1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide

: 294862-42-3
1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

Guidance literature:: 3-(4-methoxyphenyl)propanoic acid; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 0.666667h;

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jm0306374

Reference yield:

: 742105-12-0
(S)-4-(6-nitroindol-1-yl)butane-1,2-diol

: 294862-42-3
1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.61 g / imidazole / dimethylformamide / 20 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.1: NaH / dimethylformamide / 1 h / 70 °C

3.2: 489 mg / dimethylformamide / 38 h / 70 °C

4.1: 94.7 percent / iron; aq. ammonium chloride / 0.67 h / 90 °C

5.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0.67 h / 20 °C

5.2: 92.5 percent / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; ammonium chloride; iron; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0306374

Reference yield:

: 294862-23-0
1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-nitroindole

: 294862-42-3
1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. HCl / tetrahydrofuran / 5 h / 20 °C

2.1: 1.61 g / imidazole / dimethylformamide / 20 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: NaH / dimethylformamide / 1 h / 70 °C

4.2: 489 mg / dimethylformamide / 38 h / 70 °C

5.1: 94.7 percent / iron; aq. ammonium chloride / 0.67 h / 90 °C

6.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0.67 h / 20 °C

6.2: 92.5 percent / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; hydrogenchloride; ammonium chloride; iron; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0306374